Chemistry and chemical reactivity 8e by kotz, terichel and townsend 2 pdf

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Chemistry and chemical reactivity 8e Chemistry and chemical reactivity 8e by kotz, terichel and townsend 2 pdf Chemistry and chemical reactivity 8e by kotz, terichel and townsend 2 pdf Chemistry and chemical reactivity 8e by kotz, terichel and townsend 2 pdf Chemistry and chemical reactivity 8e by kotz, terichel and townsend 2 pdf Chemistry and chemical reactivity 8e by kotz, terichel and townsend 2 pdf Chemistry and chemical reactivity 8e by kotz, terichel and townsend 2 pdf 10.3  Alcohols, Ethers, and Amines 461 Think about Your Answer ​Additional structural isomers with the formula C5H11OH are possible in which the longest carbon chain has three C atoms (one isomer) or four C atoms (four isomers) Check Your Understanding ​ Draw the structure of 1-butanol and alcohols that are structural isomers of the compound Properties of Alcohols Methane, CH4, is a gas (boiling point, −161 °C) with low solubility in water Methanol, CH3OH, by contrast, is a liquid that is miscible with water in all proportions The boiling point of methanol, 65 °C, is 226 °C higher than the boiling point of methane What a difference the addition of a single atom into the structure can make in the properties of simple molecules! Alcohols are related to water, with one of the H atoms of H2O being replaced by an organic group If a methyl group is substituted for one of the hydrogens of water, methanol results Ethanol has a OC2H5 (ethyl) group, and propanol has a OC3H7 (propyl) group in place of one of the hydrogens of water Viewing alcohols as related to water also helps in understanding their properties The two parts of methanol, the OCH3 group and the OOH group, contribute to its properties For example, methanol will burn, a property associated with hydrocarbons On the other hand, its boiling point is more like that of water The temperature at which a substance boils is related to the forces of attraction between molecules, called intermolecular forces: The stronger the attractive, intermolecular forces in a sample, the higher the boiling point (▶ Section 12.4) These forces are particularly strong in water, a result of the polarity of the OOH group in this molecule (◀ Section 8.8) Methanol is also a polar molecule, and it is the polar OOH group that leads to a high boiling point In contrast, methane is nonpolar and its low boiling point is the result of weak intermolecular forces It is also possible to explain the differences in the solubility of methane, methanol, and other alcohols in water (Figure 10.9) The solubility of methanol and ethylene glycol is conferred by the polar OOH portion of the molecule Methane, which is nonpolar, has low water-solubility Methanol is often added to automobile gasoline tanks in the winter to prevent water in the fuel lines from freezing It is soluble in water and lowers the water’s freezing point nonpolar hydrocarbon portion polar portion Ethylene glycol is used in automobile radiators It is soluble in water, and lowers the freezing point and raises the boiling point of the water in the cooling system (▶ Section 14.4.) © Cengage Learning/Charles D Winters © Cengage Learning/Charles D Winters polar portion Ethylene glycol, a major component of automobile antifreeze, is completely miscible with water Figure 10.9  Properties and uses of two alcohols, methanol and ethylene glycol kotz_48288_10_0438-0489.indd 461 11/19/10 9:46 AM 462 c h a p t er 10   Carbon: Not Just Another Element As the size of the alkyl group in an alcohol increases, the alcohol boiling point rises, a general trend seen in families of similar compounds and related to molar mass (see Table 10.7) The solubility in water in this series decreases Methanol and ethanol are completely miscible in water, whereas 1-propanol is moderately water-soluble; 1-butanol is less soluble than 1-propanol With an increase in the size of the hydrocarbon group, the organic group (the nonpolar part of the molecule) has become a larger fraction of the molecule, and properties associated with nonpolarity begin to dominate Space-filling models show that in methanol, the polar and nonpolar parts of the molecule are approximately similar in size, but in 1-butanol the OOH group is less than 20% of the molecule The molecule is less like water and more “organic.” Electrostatic potential surfaces amplify this point nonpolar hydrocarbon polar portion portion nonpolar hydrocarbon portion methanol polar portion 1-butanol Amines It is often convenient to think about water and ammonia as being similar molecules: They are the simplest hydrogen compounds of adjacent second-period elements Both are polar and exhibit some similar chemistry, such as protonation (to give H3O+ and NH4+) and deprotonation (to give OH− and NH2−) This comparison of water and ammonia can be extended to alcohols and amines Alcohols have formulas related to water in which one hydrogen in H2O is replaced with an organic group (ROOH) In organic amines, one or more hydrogen atoms of NH3 are replaced with an organic group Amine structures are similar to ammonia’s structure; that is, the geometry about the N atom is trigonal pyramidal Amines are categorized based on the number of organic substituents as primary (one organic group), secondary (two organic groups), or tertiary (three organic groups) As examples, consider the three amines with methyl groups: CH3NH2, (CH3)2NH, and (CH3)3N kotz_48288_10_0438-0489.indd 462 CH3NH2 (CH3)2NH (CH3)3N primary amine methylamine secondary amine dimethylamine tertiary amine trimethylamine 11/19/10 9:46 AM 10.3 Alcohols, Ethers, and Amines 463 Properties of Amines Amines usually have offensive odors You know what the odor is if you have ever smelled decaying fish Two appropriately named amines, putrescine and cadaverine, add to the odor of urine, rotten meat, and bad breath H2NCH2CH2CH2CH2NH2 H2NCH2CH2CH2CH2CH2NH2 putrescine 1,4-butanediamine cadaverine 1,5-pentanediamine The smallest amines are water-soluble, but most amines are not All amines are bases, however, and they react with acids to give salts, many of which are water-soluble As with ammonia, the reactions involve adding H+ to the lone pair of electrons on the N atom This is illustrated by the reaction of aniline (aminobenzene) with H2SO4 to give anilinium hydrogen sulfate C6H5NH2(aq) + H2SO4(aq) Electrostatic potential surface for methylamine The surface for methylamine shows that this water-soluble amine is polar with the partial negative charge on the N atom C6H5NH3+(aq) + HSO4−(aq) HC HC H C N H2C CH C CH CH2 N CH2 CH3 nicotine aniline anilinium ion The facts that an amine can be protonated and that the proton can be removed again by treating the compound with a base have practical and physiological importance Nicotine in cigarettes is normally found in the protonated form (This watersoluble form is often also used in insecticides.) Adding a base such as ammonia removes the H+ ion to leave nicotine in its “free-base” form NicH22+(aq) + NH3(aq) → Nic(aq) + NH4 (aq) + In this form, nicotine is much more readily absorbed by the skin and mucous membranes, so the compound is a much more potent poison H+ H+ Nicotine, an amine Two nitrogen atoms in the nicotine molecule can be protonated, which is the form in which nicotine is normally found The protons can be removed, by treating it with a base This “free-base” form is much more poisonous and addictive revIeW & cHecK FOr SectIOn 10.3 How many different compounds (alcohols and ethers) exist with the molecular formula C4H10O? (a) 2 (b) 2-propanol (c) (b) 2-butanol (d) more than 2-methyl-3-pentanol (d) 1,2-propanediol What is the hybridization of nitrogen in dimethylamine? (a) sp3 (c) (b) sp2 4 Which of the following compounds is not chiral, that is, which does not possess a carbon atom attached to four different groups? (a) (c) sp (d) nitrogen is not hybridized What chemical reagent will react with the ethylammonium ion [CH3CH2NH3]+ to form ethylamine? (a) kotz_48288_10_0438-0489.indd 463 O2 (b) N2 (c) H2SO4 (d) NaOH 11/19/10 9:46 AM 464 c h a p t er 10 Carbon: Not Just Another Element 10.4 CompoundswithaCarbonylgroup Formaldehyde, acetic acid, and acetone are among the organic compounds referred to in previous examples These compounds have a common structural feature: Each contains a trigonal-planar carbon atom doubly bonded to an oxygen The CPO group is called the carbonyl group, and these compounds are members of a large class of compounds called carbonyl compounds CASE STUDY An Awakening with L-DOPA From about 1917 to 1928, millions of people worldwide were affected by a condition known as encephalitis lethargica, or a form of sleeping sickness Those who suffered from the condition were in a state of semi-consciousness that lasted for decades In his book, Awakenings, Oliver Sacks wrote about treating a patient with the compound L-DOPA, which “was started in early March 1969 and raised by degrees to 5.0 g a day Little effect was seen for two weeks, and then a sudden ‘conversion’ took place Mr L enjoyed a mobility, a health, and a happiness which he had not known in thirty years Everything about him filled with delight: he was like a man who had awoken from a nightmare or a serious illness ” The compound is also a derivative of phenylalanine, one of many naturally occurring alpha-amino acids that play such an important role in protein formation and other natural processes L-DOPA also illustrates why chiral molecules are so interesting to chemists: Only the “levo” enantiomer is physiologically active The enantiomer that rotates polarized light in the opposite direction has no biological function Interestingly, both L-DOPA and dopamine are closely related to another amine, epinephrine This is sometimes referred to as adrenaline, the hormone that is released from the adrenal glands when there is an emergency or danger threatens COLUMBIA/THE KOBAL COLLECTION/ GOLDMAN, LOUIS epinephrine or adrenaline, C9H13NO3 Robert DeNiro as Leonard Lowe and Robin Williams as Malcolm Sayer, a fictionalized portrayal of Oliver Sacks, in the movie version of Awakenings If you have read the book or have seen the movie of the same name, you know that Mr L eventually could not tolerate the treatment, but that Sacks treated many others who benefitted from it L-DOPA is now widely used in the treatment of another condition, Parkinson’s disease, a degenerative disorder of the central nervous system L-DOPA or L-dopamine (L-3,4-dihydroxy– phenylalanine) is chiral The symbol L stands for “levo,” which means a solution of the compound rotates polarized light to the left kotz_48288_10_0438-0489.indd 464 Questions: L-DOPA, C9H11NO4, a treatment for Parkinson’s disease When L-DOPA is ingested, it is metabolized to dopamine in a process that removes the carboxylic acid group, OCO2H, and it is dopamine that is physiologically active Dopamine is a neurotransmitter that occurs in a wide variety of animals L-DOPA is chiral What is the center of chirality in the molecule? Is either dopamine or epinephrine chiral? If so, what is the center of chirality? If you are treated with 5.0 g of L-DOPA, what amount (in moles) is this? Answers to these questions are available in Appendix N References: Oliver Sacks, Awakenings, Vintage Books, New York, 1999 N Angier, “A Molecule of Motivation, Dopamine Excels at its Task,” New York Times, October 27, 2009 dopamine, C8H11NO2, a neurotransmitter 11/19/10 9:46 AM 10.4  Compounds with a Carbonyl Group Primary alcohol: ethanol O CH3 C H carbonyl group formaldehyde acetic acid acetone CH2O aldehyde CH3CO2H carboxylic acid CH3COCH3 ketone • • • • C OH H Secondary alcohol: 2-propanol CH3 In this section, we will examine five groups of carbonyl compounds (Table 10.6, page 459): • 465 H C OH CH3 Aldehydes (RCHO) have an organic group (OR) and an H atom attached to a carbonyl group Ketones (RCOR′) have two OR groups attached to the carbonyl carbon; they may be the same groups, as in acetone, or different groups Carboxylic acids (RCO2H) have an OR group and an OOH group attached to the carbonyl carbon Esters (RCO2R′) have OR and OOR′ groups attached to the carbonyl carbon Amides (RCONR2′, RCONHR′, and RCONH2) have an OR group and an amino group (ONH2, ONHR, ONR2) bonded to the carbonyl carbon Tertiary alcohol: 2-methyl-2-propanol CH3 H3C C OH CH3 Aldehydes, ketones, and carboxylic acids are oxidation products of alcohols and, indeed, are commonly made by this route The product obtained through oxidation of an alcohol depends on the alcohol’s structure, which is classified according to the number of carbon atoms bonded to the C atom bearing the OOH group Primary alcohols have one carbon and two hydrogen atoms attached, whereas secondary alcohols have two carbon atoms and one hydrogen atom attached Tertiary alcohols have three carbon atoms attached to the C atom bearing the OOH group A primary alcohol is oxidized in two steps, first to an aldehyde and then to a carboxylic acid: R CH2 oxidizing agent OH primary alcohol O R C H O oxidizing agent R C OH carboxylic acid aldehyde H H H C C H H oxidizing agent OH(ℓ) H H O C C OH(ℓ) H ethanol acetic acid Acids have a sour taste The word “vinegar” (from the French vin aigre) means sour wine A device to test one’s breath for alcohol relies on the oxidation of ethanol (Figure 10.10) Oxidation of a secondary alcohol produces a ketone: OH R C R′ oxidizing agent O R C R′ H ( R and secondary alcohol ketone R′ are organic groups They may be the same or different.) Common oxidizing agents used for these reactions are reagents such as KMnO4 and K2Cr2O7 (◀ Table 3.3) kotz_48288_10_0438-0489.indd 465 © Cengage Learning/Charles D Winters For example, the air oxidation of ethanol in wine produces wine vinegar, the most important ingredient of which is acetic acid Figure 10.10  Alcohol tester This device for testing a person’s breath for the presence of ethanol relies on the oxidation of the alcohol If present, ethanol is oxidized by potassium dichromate, K2Cr2O7, to acetaldehyde, and then to acetic acid The yellow-orange dichromate ion is reduced to green Cr3+(aq), the color change indicating that ethanol was present 11/19/10 9:47 AM 466 c h a p t er 10   Carbon: Not Just Another Element Finally, tertiary alcohols not react with the usual oxidizing agents oxidizing agent (CH3)3COH no reaction Aldehydes and Ketones Aldehydes and ketones can have pleasant odors and are often used in fragrances Benzaldehyde is responsible for the odor of almonds and cherries; cinnamaldehyde is found in the bark of the cinnamon tree; and the ketone 4-(p-hydroxyphenyl)-2butanone is responsible for the odor of ripe raspberries (a favorite of the authors of this book) Table 10.8 lists several simple aldehydes and ketones benzaldehyde, C6H5CHO trans-cinnamaldehyde, C6H5CHPCHCHO Aldehydes and ketones are the oxidation products of primary and secondary alcohols, respectively The reverse reactions—reduction of aldehydes to primary alcohols and reduction of ketones to secondary alcohols—are also known Commonly used reagents for such reductions are NaBH4 and LiAlH4, although H2 is used on an industrial scale OH O R C H NaBH4 or LiAlH4 R C H H aldehyde primary alcohol OH O R C R NaBH4 or LiAlH4 R C R H ketone secondary alcohol Table 10.8  Simple Aldehydes and Ketones Structure Common Name Systematic Name BP (°C) Formaldehyde Methanal Acetaldehyde Ethanal 20 Acetone Propanone 56 Methyl ethyl ketone Butanone 80 Diethyl ketone 3-Pentanone O HCH −19 © Cengage Learning/Charles D Winters O CH3CH O CH3CCH3 O CH3CCH2CH3 Aldehydes and odors The odors of almonds and cinnamon are due to aldehydes, whereas the odor of fresh raspberries comes from a ketone kotz_48288_10_0438-0489.indd 466 O CH3CH2CCH2CH3 102 11/19/10 9:47 AM 467 10.4 Compounds with a Carbonyl Group Carboxylic Acids Acetic acid is the most common and most important carboxylic acid For many years, acetic acid was made by oxidizing ethanol produced by fermentation Now, however, acetic acid is generally made by combining carbon monoxide and methanol in the presence of a catalyst: CH3OH(ℓ) + CO(g) catalyst CH3CO2H(ℓ) methanol acetic acid About billion kilograms of acetic acid are produced annually in the United States for use in plastics, synthetic fibers, and fungicides Many organic acids are found naturally (Table 10.9) Acids are recognizable by their sour taste (Figure 10.11) and are found in common foods: Citric acid in fruits, acetic acid in vinegar, and tartaric acid in grapes are just three examples Some carboxylic acids have common names derived from the source of the acid (Table 10.9) Because formic acid is found in ants, its name comes from the Latin word for ant ( formica) Butyric acid gives rancid butter its unpleasant odor, and the name is related to the Latin word for butter (butyrum) The systematic names of acids (Table 10.10) are formed by dropping the “-e” on the name of the corresponding alkane and adding “-oic” (and the word “acid”) A CLOSER LOOK Glucose and Other Sugars © Cengage Learning/Charles D Winters Glucose, the most common, naturally occurring carbohydrate, has the alcohol and carbonyl functional groups As their name implies, formulas of most carbohydrates can be written as though they are a combination of carbon and water, Cx(H2O)y Thus, the formula of glucose, C6H12O6, is equivalent to C6(H2O)6 This compound is a sugar, or, more accurately, a monosaccharide Carbohydrates are polyhydroxy aldehydes or ketones Glucose is an interesting molecule that exists in three different isomeric forms Two of the isomers contain six-member rings; the third isomer features a chain structure In solution, the three forms rapidly interconvert Notice that glucose is a chiral molecule In the chain structure, four of the carbon atoms are bonded to four different groups In nature, glucose occurs in just one of its enantiomeric forms; thus, a solution of glucose rotates polarized light Home test for glucose kotz_48288_10_0438-0489.indd 467 H HO OH HO H 3H O OH H H HO H H OH H Knowing glucose’s structure allows one to predict some of its properties With five polar OOH groups in the molecule, glucose is, not surprisingly, soluble in water The aldehyde group is susceptible to chemical oxidation to form a carboxylic acid, and detection of glucose (in urine or blood) takes advantage of this fact Diagnostic tests for glucose involve oxidation with subsequent detection of the products Glucose is in a class of sugar molecules called hexoses, monosaccharides having six carbon atoms 2-Deoxyribose, the sugar in the backbone of the DNA molecule, is a pentose, a molecule with five carbon atoms O H H OH OH HO HO OH H H 3H H deoxyribose, a pentose, part of the DNA backbone OH OH H ␤-D-glucose Glucose and other monosaccharides serve as the building blocks for larger carbohydrates Sucrose, or “table sugar,” is a disaccharide and is formed from a molecule of glucose and a molecule of fructose, another monosaccharide Starch is a polymer composed of many monosaccharide units H OH HO H HO O H H OH CH2OH O H ␣-D-glucose H HO fructose H O H open-chain form ␣-D-glucose HO H CHO OH H OH OH CH2OH O OH H H CH2OH The structure of sucrose Sucrose is formed from α-d-glucose and fructose An ether linkage is formed by loss of H2O from two OOH groups 11/19/10 9:47 AM 468 c h a p t er 10   Carbon: Not Just Another Element Table 10.9  Some Naturally Occurring Carboxylic Acids © Cengage Learning/Charles D Winters Name Structure Natural Source CO2H Benzoic acid Berries OH Citric acid HO2C CH2 C CH2 CO2H Citrus fruits CO2H Lactic acid H3C CH CO2H Sour milk OH Malic acid HO2C CH2 CH CO2H Apples OH Formic acid, HCO2H This acid puts the sting in ant bites Oleic acid CH3(CH2)7 Oxalic acid HO2C CH CH Stearic acid CH3(CH2)16 CO2H Tartaric acid HO2C CH CH OH OH (CH2)7 CO2H CO2H Vegetable oils Rhubarb, spinach, cabbage, tomatoes Animal fats CO2H Grape juice, wine Because of the substantial electronegativity of oxygen, the two O atoms of the carboxylic acid group are slightly negatively charged, and the H atom of the OOH group is positively charged This charge distribution has several important implications: • • The polar acetic acid molecule dissolves readily in water, which you already know because vinegar is an aqueous solution of acetic acid (Acids with larger organic groups are less soluble, however.) The hydrogen of the OOH group is the acidic hydrogen As noted in Chapter 3, acetic acid is a weak acid in water, as are most other organic acids © Cengage Learning/Charles D Winters Carboxylic acids undergo a number of reactions Among these is the reduction of the acid (with reagents such as LiAlH4 or NaBH4) first to an aldehyde and then Table 10.10  Some Simple Carboxylic Acids Structure Common Name Systematic Name BP (°C) Formic acid Methanoic acid 101 Acetic acid Ethanoic acid 118 Propionic acid Propanoic acid 141 Butyric acid Butanoic acid 163 Valeric acid Pentanoic acid 187 O HCOH Figure 10.11   Acetic acid in bread Acetic acid is produced in bread leavened with the yeast Saccharomyces exigus Another group of bacteria, Lactobacillus sanfrancisco, contributes to the flavor of sourdough bread These bacteria metabolize the sugar maltose, excreting acetic acid and lactic acid, CH3CH(OH)CO2H, thereby giving the bread its unique sour taste kotz_48288_10_0438-0489.indd 468 O CH3COH O CH3CH2COH O CH3(CH2)2COH O CH3(CH2)3COH 11/19/10 9:47 AM 10.4  Compounds with a Carbonyl Group to an alcohol For example, acetic acid is reduced first to acetaldehyde and then to ethanol CH3CO2H LiAlH4 acetic acid LiAlH4 CH3CHO CH3CH2OH acetaldehyde ethanol 469 H O H C C O H acidic H atom −␦ H Yet another important aspect of carboxylic acid chemistry is the reaction with bases to give carboxylate anions For example, acetic acid reacts with hydroxide ions to give acetate ions and water −␦ +␦ carboxylic acid group CH3CO2H(aq) + OH−(aq) → CH3CO2−(aq) + H2O(ℓ) Esters Carboxylic acids (RCO2H) react with alcohols (R′OH) to form esters (RCO2R′) in an esterification reaction (These reactions are generally carried out in the presence of strong acids because acids speed up the reaction.) O O RC O H + R′ carboxylic acid O H H3O+ alcohol O R′ + H2O ester O O CH3COH + CH3CH2OH acetic acid RC H3O+ CH3COCH2CH3 + H2O ethanol ethyl acetate When a carboxylic acid and an alcohol react to form an ester, the OR′ group of the alcohol ends up as part of the ester (as shown above) This fact is known because of isotope labeling experiments If the reaction is run using an alcohol in which the alcohol oxygen is 18O, all of the 18O ends up in the ester molecule Table 10.11 lists a few common esters and the acid and alcohol from which they are formed The two-part name of an ester is given by (1) the name of the hydrocarbon group from the alcohol and (2) the name of the carboxylate group derived from the acid name by replacing “-ic” with “-ate.” For example, ethanol (commonly called ethyl alcohol) and acetic acid combine to give the ester ethyl acetate An important reaction of esters is their hydrolysis (literally, reaction with water), a reaction that is the reverse of the formation of the ester The reaction, generally done in the presence of a base such as NaOH, produces the alcohol and a sodium salt of the carboxylic acid: O RCOR′ + NaOH ester portion from acetic acid portion from ethanol ethyl acetate, an ester CH3CO2CH2CH3 O heat in water CH3COCH2CH3 + NaOH RCO − Na+ + R′OH carboxylate salt alcohol O O ethyl acetate Acetic acid The H atom of the carboxylic acid group (OCO2H) is the acidic proton of this and other carboxylic acids heat in water CH3CO − Na+ + CH3CH2OH sodium acetate ethanol The carboxylic acid can be recovered if the sodium salt is treated with a strong acid such as HCl: O CH3CO −Na+(aq) + HCl(aq) sodium acetate kotz_48288_10_0438-0489.indd 469 O CH3COH(aq) + NaCl(aq) acetic acid 11/19/10 9:47 AM c h a p t er 10   Carbon: Not Just Another Element © Cengage Learning/Charles D Winters 470 Table 10.11  Some Acids, Alcohols, and Their Esters Acid Alcohol Ester CH3 Esters Many fruits such as bananas and strawberries as well as consumer products (here, perfume and oil of wintergreen) contain esters Odor of Ester O CH3 CH3CO2H CH3CHCH2CH2OH CH3COCH2CH2CHCH3 acetic acid 3-methyl-1-butanol 3-methylbutyl acetate Banana O CH3CH2CH2CO2H CH3CH2CH2CH2OH CH3CH2CH2COCH2CH2CH2CH3 butanoic acid 1-butanol butyl butanoate Pineapple O CH3CH2CH2COCH2 CH2OH CH3CH2CH2CO2H butanoic acid benzyl alcohol Rose benzyl butanoate Unlike the acids from which they are derived, esters often have pleasant odors (Table 10.11) Typical examples are methyl salicylate, or “oil of wintergreen,” and benzyl acetate Methyl salicylate is derived from salicylic acid, the parent compound of aspirin O COH + CH3OH COCH3 + H2O OH H O O OH salicylic acid C methanol methyl salicylate, oil of wintergreen O O C CH3 O Benzyl acetate, the active component of “oil of jasmine,” is formed from benzyl alcohol (C6H5CH2OH) and acetic acid The chemicals are inexpensive, so synthetic jasmine is a common fragrance in less expensive perfumes and toiletries O Aspirin, a commonly used analgesic It is based on benzoic acid with an acetate group, OO2CCH3, in the ortho position Aspirin has both carboxylic acid and ester functional groups O CH3COH + acetic acid CH2OH + H2O CH3COCH2 benzyl alcohol benzyl acetate oil of jasmine Amides An acid and an alcohol react by loss of water to form an ester In a similar manner, another class of organic compounds—amides—form when an acid reacts with an amine, again with loss of water O R C R′ OH + H carboxylic acid N amine R′ R O R′ C N R′ + H2O amide Amides have an organic group and an amino group (ONH2, ONHR′, or ONR′R) attached to the carbonyl group The C atom involved in the amide bond has three bonded groups and no lone pairs around it We would predict it should be sp hybridized with trigonal- kotz_48288_10_0438-0489.indd 470 11/19/10 9:47 AM I-18 i n d e x / glossary millimeter of mercury (mm Hg)  A common unit of pressure, defined as the pressure that can   support a 1-millimeter column of mercury;   760 mm Hg = atm, 510, A-7t mineral oil, density of, 43 minerals,  analysis of, 167 clay, 987 silicate, 986 solubility of, 831 mischmetal, 66 miscibility, 621 mixture(s)  A combination of two or more substances in which each substance retains its identity, 9–10 analysis of, 166–172 gaseous, partial pressures in, 524–527 separation by chromatography, 581 mobile phase, in chromatography, 581 models, molecular, 68 moderator, nuclear, 1058 Mohr method, 187 Moisson, Henri, 1001 molal boiling point elevation constant (Kbp), 632 molality (m)  The number of moles of solute per kilogram of solvent, 618 molar absorptivity, 191 molar enthalpy of vaporization (∆vapH°), relation to molar enthalpy of condensation, 566 molar heat capacity, 212t, 213 values of, A-14t molar mass (M)  The mass in grams of one mole of particles of any substance, 80 calculation from colligative properties, 637 determination by titration, 185 effusion rate and, 532 enthalpy of vaporization and, 567 from ideal gas law, 521 molecular speed and, 530 polarizability and, 559 molar volume, standard, 519 molarity (M)  The number of moles of solute per liter of solution, 173, 618 mole (mol)  The SI base unit for amount of substance, 80, A-10 conversion to mass units, 80 of reaction, 165, 224 mole fraction (X)  The ratio of the number of moles of one substance to the total number of moles in a mixture of substances, 526, 618 in Raoult’s law, 630 molecular compound(s)  A compound formed by the combination of atoms without significant ionic character, 69, 78–79 See also covalent compound(s) as Brønsted acids and bases, 758 as Lewis acids, 794 of main group elements, 963 as nonelectrolytes, 121 molecular formula  A written formula that expresses the number of atoms of each type within one molecule of a compound, 66 determining, 85–94 empirical formula and, 87 relation to empirical formula, 88 molecular geometry  The arrangement in space of the central atom and the atoms directly attached to it, 366 hybrid orbitals and, 405 molecular polarity and, 375–381, 390t multiple bonds and, 368–370 kotz_48288_25_Index_I01-I30.indd 18 molecular models, 68 molecular orbital(s), bonding and antibonding, 418 from atomic p orbitals, 421 highest occupied (HOMO), 421 lowest unoccupied (LUMO), 421 molecular orbital theory  A model of bonding in which pure atomic orbitals combine to produce molecular orbitals that are delocalized over two or more atoms, 401, 416–427, 1038 for metals and semiconductors, 594–598 resonance and, 424 molecular polarity, 375–381, 390t intermolecular forces and, 550 of lipids, 501 miscibility and, 621 of surfactants, 645 molecular solid(s)  A solid formed by the condensation of covalently bonded molecules, 601 solubilities of, 622 molecular structure, acid-base properties and, 787–791 bonding and, 344–390 entropy and, 867 VSEPR model of, 364–370 molecular weight See molar mass molecularity  The number of particles colliding in an elementary step, 698 reaction order and, 699 molecule(s)  The smallest unit of a compound that retains the composition and properties of that compound, 12, 66 calculating mass of, 84 collisions of, reaction rate and, 689–693 early definition of, 337 molar mass of, 82 nonpolar, interactions of, 559–562 polar, interactions of, 552 shapes of, 364–370 speeds in gases, 529 volume of, 534 Molina, Mario, 951 molybdenite, 1020 molybdenum, generation of technetium from, 1084 monatomic ion(s)  An ion consisting of one atom bearing an electric charge, 70 naming, 74–75 Mond, Ludwig, 1047 Mond process, 1048 monodentate ligands, 1028 monomer(s)  The small units from which a polymer is constructed, 473 monoprotic acid(s)  A Brønsted acid that can donate one proton, 759 monosaccharides, 467 Montreal Protocol, in CFC reduction, 952 moon, rock samples analyzed, 1086 mortar, lime in, 976, 977 Moseley, Henry G J , 60, 340 Müller, Karl, 155 Mulliken, Robert S., 399, 401 multiple bonds, 348 molecular geometry and, 368–370 in resonance structures, 356 valence bond theory of, 411–416 mummy, 1, 92 mussels, glue from, 481, 666 mutation, of retroviruses, 501 Mylar, 478 myoglobin, 1032 myristic acid, 489 n-type semiconductor, 598 naming, of alcohols, 459t of alcohols, A-17 of aldehydes and ketones, 466t, A-17 of alkanes, 444t, 446, A-15 of alkenes, 449, A-16 of alkynes, 452t, A-16 of anions and cations, 74–75 of aromatic compounds, A-16 of benzene derivatives, A-16 of binary nonmetal compounds, 79 of carboxylic acids, 468, A-17 of coordination compounds, 1031 of esters, 469, 470t, A-17 of ionic compounds, 75 of substituted alkanes, 452 nanometer, 27 nanotechnology, 667 nanotubes, carbon, 667 naphthalene, enthalpy of formation, 244 melting point, 14 solubility in benzene, 622 structure of, 454 National Institute of Standards and Technology (NIST), 30, 233 natural gas, 258 energy of combustion, 257t natural logarithms, A-2 neodymium, magnetism of, 329, 333 neon, density of, 23 line emission spectrum of, 273, 294 mass spectrum of, 55 neptunium, 1077 Nernst, Walther, 921 Nernst equation  A mathematical expression that relates the potential of an electrochemical cell to the concentrations of the cell reactants and products, 921 Nestlé, Henry, 438 net ionic equation(s)  A chemical equation involving only those substances undergoing chemical changes in the course of the   reaction, 126 of strong acid–strong base reactions, 132 network solid(s)  A solid composed of a network of covalently bonded atoms, 601 bonding in, 596 silicon dioxide, 985 solubilities of, 623 neurotransmitter, 464 neutral buoyancy, 547 neutral solution  A solution in which the concentrations of hydronium ion and hydroxide ion are equal, 761 neutralization reaction(s)  An acid–base reaction that produces a neutral solution of a salt and water, 133, 774 neutrino(s)  A massless, chargeless particle emitted by some nuclear reactions, 1064 neutron(s)  An electrically neutral subatomic particle found in the nucleus, 51 bombardment with, 1077 conversion to electron and proton, 1061 demonstration of, 343 discovery of, 1075 in nuclear reactor, 1058 nuclear stability and, 1065 neutron activation analysis, 1086 neutron capture reactions, 1077 newton (N)  The SI unit of force, N = kg ⋅ m/s2, A-6, A-11 Newton, Isaac, 336 11/22/10 11:29 AM nickel, as catalyst in diamond synthesis, 893 coordination complex with ammonia, 1028 density of, 45, 48 in memory metal, 1016 reaction with oxygen, 890 nickel-cadmium (Ni-cad) battery, 911 nickel(II) carbonate, reaction with sulfuric acid, 137 nickel carbonyl, 1047 decomposition of, temperature and spontaneity, 882 nickel(II) chloride hexahydrate, 96, 1026, 1027 nickel(II) complexes, stability, 843 nickel(II) formate, 330 nickel(II) ion, light absorption by, 188 reaction with dimethylglyoxime (DMG), 154, 651 nickel-metal hydride battery, 894 nickel(II) nitrate, reaction with ammonia and ethylenediamine, 754 nickel(II) oxide, reaction with chlorine trifluoride, 543 nickel(II) sulfide, quantitative analysis of, 168 nickel tetracarbonyl, substitution of, 717 nicotinamide adenine dinucleotide (NADH), 505 nicotine, structure of, 463, 795 nicotinic acid, structure of, 803 nitinol, 1016 nitramide, decomposition of, 715 nitrate ion, concentration in aquarium, 991 molecular geometry of, 370 resonance structures of, 357, 789 structure of, 352, 353t nitration, of benzene, 456 nitric acid, 993 as oxidizing agent, 142t pH of, 180 production by Ostwald process, 993 reaction with aluminum, 983 reaction with copper, 142 reaction with metals, 994 strength of, 787 structure of, 99, 352, 353t nitric oxide See nitrogen monoxide nitride(s), 989 nitrification, by bacteria, 991 nitrite ion, concentration in aquarium, 991 linkage isomers containing, 1035 molecular geometry of, 370 resonance structures of, 358 nitrito complex, 1035 nitro complex, 1035 nitrocellulose, 251 nitrogen, abundance of, 989 bond enthalpy of triple bond, 989 bond order in, 382 chemistry of, 989–994 compounds of, hydrogen bonding in, 554 with hydrogen, 990 fixation of, 64, 948 Henry’s law constant, 626t Lewis structures involving, 350–351 liquid, 513, 989 liquid and gas volumes, 550 molecular compounds of, 964 molecular orbital configuration of, 421 oxidation numbers of, 990 oxides of, 992 reaction with hydrogen, 522 reaction with oxygen, 736, 744 kotz_48288_25_Index_I01-I30.indd 19 inde x / g los sa ry in testing food for protein content, 565 transmutation to oxygen, 1075 nitrogen cycle, 949 nitrogen dioxide, 948, 992 decomposition of, 710 dimerization of, 363, 364, 729, 743, 993 in formation of atmospheric ozone, 950 free radical, 362 production of hydroxyl radicals by, 363 reaction with carbon monoxide, 679, 703 reaction with fluorine, 701 reaction with water, 135 nitrogen monoxide, 948, 992 air pollution and, 261 biological roles of, 363 enthalpy of formation, 243 free radical, 362 oxidation of, 241 reaction with bromine, 698, 709 reaction with chlorine, 676 reaction with oxygen, mechanism of, 704–706 reaction with ozone, 727 nitrogen narcosis, 534 nitrogen oxides, in atmosphere, 948 nitrogen trifluoride, molecular polarity of, 380 structure of, 352 nitrogenase, 1018 nitrogenous base(s), 497 nitroglycerin, 251, 460 decomposition of, 235 nitromethane, vapor pressure of, 576 nitronium ion, Lewis structure of, 350 m-nitrophenol, structure of, 801 nitrosyl bromide, decomposition of, 750, 753 formation of, 698, 709 rate of formation of, 709 nitrosyl chloride, rate of decomposition of, 672 nitrosyl ion, 430 nitrous acid, 993 strength of, 787 nitrous oxide See dinitrogen oxide nitryl chloride, electrostatic potential map of, 396 nitryl fluoride, 714 Nobel, Alfred, 460 noble gas(es)  The elements in Group 8A of the periodic table, 65, 948 compounds of, 361, 400 discovery of, 109 electron configuration of, 71, 309, 347, 962 in ions, 325 noble gas notation  An abbreviated form of spdf notation that replaces the completed electron shells with the symbol of the corresponding noble gas in brackets, 307 noble metals, 994 nodal surface  A surface on which there is zero probability of finding an electron, 285, 286 node(s)  A point of zero amplitude of a wave, 268 nonaqueous solvents, acid strength in, 805 nonbonding electrons See lone pair(s) nonelectrolyte  A substance that dissolves in water to form an electrically nonconducting solution, 120, 121 nonequilibrium conditions, reaction quotient at, 727 reaction quotient at, 921 nonideal gas, 534 nonideal solution, 630 I-19 nonmetal(s)  An element characterized by a lack of metallic properties, 61 anions formed by, 71 binary compounds of, 79 electronegativity of, 372 nonpolar covalent bond  A covalent bond in which there is equal sharing of the bonding electron pair, 371 nonpolar molecules, 378 interactions of, 559–562 nonrenewable energy resources, 257 nonspontaneous reaction, 859 See also reactantfavored reaction(s) normal boiling point  The boiling point when the external pressure is atm, 571 for common compounds, 567t northwest–southeast rule  A product-favored reaction involves a reducing agent below and to the right of the oxidizing agent in the table of standard reduction potentials, 917 novocaine, 801 nuclear binding energy, 1067–1070 nuclear charge, effective, 304, 305t, 312 nuclear chemistry, 1058–1094 nuclear energy, 1079 nuclear fission, 1078 nuclear fusion, 1080 nuclear magnetic resonance (NMR), 291 nuclear magnetic resonance (NMR) spectrometer, 166 nuclear medicine, 1083 nuclear reaction(s)  A reaction involving one or more atomic nuclei, resulting in a change in the identities of the isotopes, 1060–1064 artificial, 1075–1078 predicting types of, 1066 rates of, 1071–1075 nuclear reactor  A container in which a controlled nuclear reaction occurs, 1079 breeder, 1091 natural, 1058, 1091 nuclear spin, quantization of, 291 nucleation, in bubble formation, 629 nucleic acid(s)  A class of polymers, including RNA and DNA, that are the genetic material of cells, 496–500 nucleon  A nuclear particle, either a neutron or a proton, 1068 nucleoside, 496 nucleotide, 496 nucleus  The core of an atom, made up of protons and neutrons, 51 demonstration of, 340 stability of, 1065–1070 Nutrient Data Laboratory site, 29 nutrition label, energy content on, 29 nylon, 479 octadecane, 581 octahedral electron-pair geometry, orbital hybridization and, 405, 410 octahedral holes, 590 octahedral molecular geometry, 365, 1034 octane, combustion of, 114 heat of combustion, 229 reaction with oxygen, 540 vapor pressure of, 576 octet, of electrons, 347 octet rule  When forming bonds, atoms of main group elements gain, lose, or share electrons to achieve a stable configuration having eight valence electrons, 348 exceptions to, 348, 360–363, 755 11/22/10 11:29 AM I-20 i n d e x /glossary odd-electron compounds, 362, 422, 992, 993 oil(s), soaps and, 645 Oklo, natural nuclear rector at, 1058 Olah, George, 805 oleic acid, 468t, 489 olivine, 986 optical fiber, 662 optical isomers  Isomers that are nonsuperimposable mirror images of each other, 441, 1036 orbital(s)  The matter wave for an allowed energy state of an electron in an atom or molecule, 282 atomic See atomic orbital(s) molecular See molecular orbital(s) orbital box diagram  A notation for the electron configuration of an atom in which each orbital is shown as a box and the number and spin direction of the electrons are shown by arrows, 301 orbital hybridization  The combination of atomic orbitals to form a set of equivalent hybrid orbitals that matches the electron pair geometry of the compound, 404–416 orbital overlap  Partial occupation of the same region of space by orbitals from two atoms, 402 relation to group number, 964 of transition elements, 1019, 1020 oxidation reaction(s), of alcohols, 465 oxidation–reduction reaction(s)  A reaction involving the transfer of one or more electrons from one species to another, 137–143, 894–945 in acidic and basic solutions, 899–902 balancing equations for, 896–903 biological, 505 in fuel cells, 262 recognizing, 141 titration using, 186 oxide ions, in glass, 661 oxides, as acids and bases, 134 oxidizing agent(s)  The substance that accepts electrons and is reduced in an oxidation–reduction reaction, 138, 896 relative strengths of, 915, 916, 919 oximes, 431 oxoacid(s), acid strengths of, 787 Lewis structures of, 352, 353t of chlorine, 1005 oxoacids, phosphorus, 996 order, bond See bond order reaction See reaction order oxoanion(s)  Polyatomic anions containing oxygen, 75 ore(s)  A sample of matter containing a desired mineral or element, usually with large quantities of impurities, 1023 as Brønsted bases, 791 Lewis structures of, 352, 353t oxy-acetylene torch, 452 oxygen, abundance of, 998 allotropes of, 65, 998 in atmosphere, 949 compounds of, hydrogen bonding in, 554 with nitrogen, 992 with phosphorus, 994, 995 concentration in water, 944 corrosion and, 1021 deprivation and sickness, 508 discovery of, 112 dissolving in water, 559 in fuel cell, 912 Henry’s law constant, 626t, 649 in iron production, 1024 isotope ratios, 58 Lewis structures involving, 350–351 molecular orbital configuration of, 421 oxidation number of, 140 as oxidizing agent, 138, 142t paramagnetism of, 289, 290, 417, 421 partial pressure and altitude, 528 from photosynthesis, 998 reaction with alkali metals, 971 reaction with alkanes, 448 reaction with calcium, 346 reaction with hemoglobin, 1032 reaction with hydrogen, 16 reaction with nitrogen, 736, 744 reaction with nitrogen monoxide, mechanism of, 704–706 toxicity in deep-sea diving, 534 oxygen difluoride, reaction with water, 394 oxygen-15, in PET imaging, 1085 oxyhemoglobin, 1032 ozone, 65, 998 in atmosphere, 950 decomposition of, 698, 712 depletion in stratosphere, 951 as disinfectant, 954 fractional bond order of, 382 molecular orbital configuration of, 424 reaction with nitrogen monoxide, 727 reaction with oxygen atoms, 394 resonance structures of, 356 solar radiation absorbed by, 528 insoluble salts in, 839 organic compounds, bonding in, 438–489 naming of, 444t, 446, A-15 organometallic chemistry, 1047–1051 orientation of reactants, effect on reaction rate, 692 Orlon, 475t ornithine, 200 orpiment, 92, 831 ions in, 69 ortho position, 455 orthophosphoric acid, 996t, 997 orthorhombic sulfur, 998 orthosilicates, 986 osmium, density of, 1018 osmosis  The movement of solvent molecules through a semipermeable membrane from a region of lower solute concentration to a region of higher solute concentration, 635 reverse, 637, 955 osmotic pressure (𝚷)  The pressure exerted by osmosis in a solution system at equilibrium, 636 Ostwald, Friedrich Wilhelm, 80 Ostwald process, 993 Ötzi the Iceman, 1, 58, 92, 1074 overlap, orbital, 402 overvoltage, 932 oxalate ion, as ligand, 1028 oxalic acid, 149, 468t molar mass of, 84 as polyprotic acid, 759t in rhubarb, 806 titration of, 182, 824 oxidation  The loss of electrons by an atom, ion, or molecule, 138 of transition metals, 1019 oxidation number(s)  A number assigned to each element in a compound in order to keep track of the electrons during a reaction, 139 formal charges and, 355 of Group 3A elements, 979 of Group 4A elements, 984 of Group 5A elements, 989, 990 of phosphorus, 997 in redox reaction, 896 kotz_48288_25_Index_I01-I30.indd 20 p-block elements, 308 molecular orbitals involving, 421, 423 p orbital(s) See atomic orbital(s) p-type semiconductor, 597 packing, in crystal lattice, 587 paint, transition metal pigments in, 1018 white lead in, 988 pairing, of electron spins, 289 pairing energy  The additional potential energy due to the electrostatic repulsion between two electrons in the same orbital, 1041 palladium, hydrogen absorption by, 264, 267 palmitic acid, 248, 489 para position, 455 paramagnetism  The physical property of being attracted by a magnetic field, 289, 421, 1041 of transition metal ions, 314, 315, 1019 parent ion, in mass spectra, 93 Parkinson’s disease, 464 parsec, 33 partial charge(s)  The charge on an atom in a molecule or ion calculated by assuming sharing of the bonding electrons proportional to the electronegativity of the atom, 371, 375 partial pressure(s)  The pressure exerted by one gas in a mixture of gases, 525 in equilibrium constant expression, 724, 726, 732 particle accelerator, 1076 particulate level  Representations of chemical phenomena in terms of atoms and molecules Also called submicroscopic level, partition chromatography, 581 parts per million (ppm), 619 pascal (Pa)  The SI unit of pressure; Pa = N/m2, 510, A-6, A-11 passive diffusion, through cell membrane, 503 path length, light absorption and, 190, 191 Pauli, Wolfgang, 301 Pauli exclusion principle  No two electrons in an atom can have the same set of four quantum numbers, 301 molecular orbitals and, 417 Pauling, Linus, 342, 343, 372 and electronegativity, 372, 399 and theory of resonance, 356 and valence bond theory, 401, 404 peanuts, heat of combustion, 248 pentane, structural isomers of, 444 1,5-pentanediol, structure of, 581 1-pentanol, structure of, 581 pentenes, isomers of, 450 pentose, 467 peptide bond, 493 peptide linkage, 434, 471 Pepto-Bismol, black tongue and, 125 composition of, 106 percent abundance  The percentage of the atoms of a natural sample of the pure element represented by a particular isotope, 54 percent composition  The percentage of the mass of a compound represented by each of its constituent elements, 85 percent error  The difference between the measured quantity and the accepted value, expressed as a percentage of the accepted value, 31 percent yield  The actual yield of a chemical reaction as a percentage of its theoretical yield, 166 perchlorate ion, structure of, 353t perchlorates, 1005 perchloric acid, structure of, 353t perchloroethylene, 574 perfluorohexane, density of, 22 11/22/10 11:29 AM perhydroxyl ion, 363 periodic table of the elements, 10, 50, 58–66, 962–966 electron configurations and, 305 historical development of, 58–59 ion charges and, 71–72 periodicity, of atomic radii, 315 of chemical properties, 58, 323–326 of electron attachment enthalpies, 320 of electronegativity, 372 of ionic radius, 322 of ionization energy, 319 periods  The horizontal rows in the periodic table of the elements, 61 Perkin, William, 426 permanganate ion, as oxidizing agent, 142t reaction with iron(II) ion, 143, 186 perovskite, structure of, 593 unit cell of, 609, 613 peroxide ion, 430 peroxides, 971 oxidation number of oxygen in, 140 peroxyacyl nitrates (PANs), 949 peroxymonocarbonate ion, 363 perspective formula, 441 pertechnate ion, 1084 pet food, adulteration of, 565 Peter, Daniel, 438 petroleum, 259 chemistry of, 458 energy of combustion, 257t Pfund series, 295 pH  The negative of the base-10 logarithm of the hydrogen ion concentration; a measure of acidity, 178–180, 760–763 in aquarium, 991 in buffer solutions, 810–817 of blood, 819 calculating equilibrium constant from, 776 calculating from equilibrium constant, 778–783 change in, during acid–base titration, 818 common ion effect and, 807–810 pH meter, 179, 925 pharmaceutical and personal care products (PPCPs), water pollution by, 957 phase change, as spontaneous process, 860 condensation, 566 heat transfer in, 216 vaporization, 565 phase diagram  A graph showing which phases of a substance exist at various temperatures and pressures, 606–607 phase transition temperature, 1016 phenanthroline, as ligand, 1028 phenol, structure of, 455 titration of, 849 phenolphthalein, structure of, 668, 827 phenyl acetate, hydrolysis of, 709 phenylalanine, structure of, 392, 485, 492 Philosopher's Stone, 336, 993 phosgene, 394 molecular polarity of, 377 phosphate ion, buffer solution of, 811t in biological buffer system, 819 resonance structures of, 359 structure of, 353t phosphate rock, 995, 996 phosphates, solubility in strong acids, 838 spectrophotometric analysis of, 204 water pollution by, 956 kotz_48288_25_Index_I01-I30.indd 21 inde x / g los sa ry phosphine, 79, 994 decomposition of, 714 rate of decomposition of, 672 phosphines, in organometallic compounds, 1049, 1054 phosphodiester group, in nucleic acids, 497 phosphoenolpyruvate (PEP), 881 phospholipids, 502 phosphoric acid, 148, 997 as polyprotic acid, 759t, 767 reaction with acetate ion, 772 structure of, 353t, 804 phosphorus, abundance of, 989 allotropes of, 64, 989, 990 chemistry of, 994–997 coordinate covalent bonds to, 361 discovery of, 336, 993 molecular compounds of, 964 oxides of, 994, 995 reaction with chlorine, 111, 112, 157 reaction with oxygen, 114 sulfides of, 995 white, 398 phosphorous acid, 996t phosphorus oxoacids, 996 phosphorus pentachloride, decomposition of, 734, 748 phosphorus pentafluoride, orbital hybridization in, 410 phosphorus trichloride, enthalpy of formation, 243 reaction with chlorine, 398 phosphoserine, structure of, 431 photocell, 271 photochemical smog, 949 photoelectric effect  The ejection of electrons from a metal bombarded with light of at least a minimum frequency, 271 photoelectron spectroscopy, 437 photolysis, flash, 719 photon(s)  A “particle” of electromagnetic radiation having zero mass and an energy given by Planck’s law, 271 photonics, 662 photosynthesis, 505, 949 photovoltaic cell, 266, 659 phthalic acid, buffer solution of, 811t physical change  A change that involves only physical properties, 15 physical properties  Properties of a substance that can be observed and measured without changing the composition of the substance,   13–15 temperature dependence of, 13 pi (𝛑) bond(s)  The second (and third, if present) bond in a multiple bond; results from sideways overlap of p atomic orbitals, 412–416 I-21 pKa  The negative of the base-10 logarithm of the acid ionization constant, 768 at midpoint of acid–base titration, 821 pH of buffer solution and, 813 planar node See atomic orbital(s) and nodal plane Planck, Max, 270, 342 Planck’s constant (h)  The proportionality constant that relates the frequency of radiation to its energy, 270 Planck’s equation, 269–272 plasma  A gas-like phase of matter that consists of charged particles, 1080 plaster of Paris, 94 plastic(s) See also polymer(s) recycling symbols, 488 plastic sulfur, 998 plating, by electrolysis, 929 platinum, 327 in cisplatin, 1047 in oxidation of ammonia, 162 platinum electrode, 907 platinum group metals, 1022 platinum hexafluoride, 430 Plexiglas, 475t plotting See graph(s) plutonium-239, fission of, 1079 pOH  The negative of the base-10 logarithm of the hydroxide ion concentration; a measure of basicity, 763 poisoning, arsenic, 92 carbon monoxide, 752, 1032 hydrogen sulfide, 999 lead, 988 polar covalent bond  A covalent bond in which there is unequal sharing of the bonding electron pair,   371 polarity, bond, 371–375 molecular, 375–381, 390t intermolecular forces and, 550 solubility of alcohols and, 461 solubility of carboxylic acids and, 468 polarizability  The extent to which the electron cloud of an atom or molecule can be   distorted by an external electric charge,   559, 580 polarized light, rotation by optically active compounds, 441, 442 polonium, 65, 338 abundance of, 998 from decay of uranium, 1062 polyacrylate polymer, in disposable diapers, 481 polyacrylonitrile, 475t polyamide(s)  A condensation polymer formed by linking monomers by amine groups, 479 polyatomic ion(s)  An ion consisting of more than one atom, 72 in benzene, 425 molecular orbital view of, 421 in organometallic compounds, 1049 in ozone, 424 pickle, light from, 297 picometer, 27 pie filling, specific heat capacity of, 213 names and formulas of, 72t, 75 oxidation numbers in, 140 polybutadiene, in ABS plastic, 478 polydentate ligands, 1028 polydimethylsiloxane, 988 piezoelectricity  The induction of an electrical current by mechanical distortion of material or vice versa, 664 polyethylene, 473, 474, 475t in disposable diapers, 481 high density (HDPE), density of, 22 structure of, 584 polyethylene terephthalate (PET), 478, 479, 487 polyisoprene, 476 polylactic acid (PLA), 478 pig iron, 1024 pigments, green chemistry of, 426 transition metals in, 1018 Piria, Raffaele, 756 pitchblende, 338, 1062, 1093 polyester(s)  A condensation polymer formed by linking monomers by ester groups, 477–479 11/22/10 11:30 AM I-22 i n d e x /glossary polymer(s)  A large molecule composed of many smaller repeating units, usually arranged in a chain, 473–481 addition, 473–477 classification of, 473 condensation, 470, 477–480 osmotic pressure of, 636, 637 silicone, 987–988 polymethyl methacrylate, 475t polypeptide, 493 polypropylene, 475t, 955 in disposable diapers, 481 polyprotic acid(s)  A Brønsted acid that can donate more than one proton, 759 ionization constants of, 767 pH of, 785 titration of, 824 polyprotic base(s)  A Brønsted base that can accept more than one proton, 759 pH of, 785 polysaccharide, 495 polystyrene, 474, 475t, 477 empirical formula of, 106 polysulfides, 1009 polytetrafluoroethylene, 475t polyvinyl acetate (PVA), 474, 475t polyvinyl alcohol, 475 polyvinyl chloride (PVC), 475t density of, 22 polyvinylidene fluoride, 955 popcorn, percent yield of, 166 porphyrin, 1032 Portland cement, 986 positron(s)  A particle having the same mass as an electron but a positive charge, 1063 emitters of, 1084 predicting emission of, 1066 positron emission tomography (PET), 1084 potassium, abundance of, 969 preparation of, 970 reaction with water, 23, 62 potassium aluminum sulfate, as coagulant, 954 potassium chlorate, decomposition of, 998 in fireworks, 279 in matches, 995 potassium chromate, reaction with hydrochloric acid, 753 potassium dichromate, 176 oxidation of alcohol by, 465 potassium dihydrogen phosphate, crystallization of, 628 potassium fluoride, dissolution of, 623 electrolysis of, 1001 potassium hydrogen phthalate, as primary standard, 199 potassium hydroxide, reaction with aluminum, 199 potassium iodide, reaction with lead nitrate, 205 potassium ions, pumping in cells, 505 potassium nitrate, 973 in fireworks, 279 potassium perchlorate, 1005 in fireworks, 279 preparation of, 201 potassium permanganate, 174 absorption spectrum of, 192 dissolution of, 865 oxidation of alcohol by, 465 reaction with iron(II) ion, 901 in redox titration, 186 potassium salts, density of, 47 kotz_48288_25_Index_I01-I30.indd 22 potassium superoxide, 971 molecular orbital configuration of, 422 reaction with carbon dioxide, 540 potassium thiocyanate, reaction with iron(II) nitrate, 753 potassium uranyl sulfate, 338 potential, of electrochemical cell, 913–921 potential energy  The energy that results from an object’s position, 16 bond formation and, 402 of electron in hydrogen atom, 274 potential ladder, 916 pounds per square inch (psi), 511, A-7 power  The amount of energy delivered per unit time, A-7 powers, calculating with logarithms, A-4 on calculator, 35 PPCPs See pharmaceutical and personal care products precipitate  A water-insoluble solid product of a reaction, usually of water-soluble reactants, 124 gelatinous, 643 precipitation reaction(s)  An exchange reaction that produces an insoluble salt, or precipitate, from soluble reactants, 123–128, 144, 828–838 solubility product constant and, 839–843 precision  The agreement of repeated measurements of a quantity with one another, 30 prefixes, for ligands, 1032 for SI units, 25, 26t, A-10 pressure  The force exerted on an object divided by the area over which the force is exerted, 510, A-6 atmospheric, altitude and, 508 constant, calorimetry at, 226 critical, 571 effect on solubility, 626 gas, volume and, 512 partial See partial pressure relation to boiling point, 571 standard, 519 units of, 510, A-6 vapor See vapor pressure pressure–volume work, 221 Priestley, Joseph, 112, 1011 primary alcohols, 465 primary battery, 908 primary colors, 1043 primary standard  A pure, solid acid or base that can be accurately weighed for preparation of a titrating reagent, 184 primary structure, of protein, 493, 494 primitive cubic (pc) unit cell, 585 principal quantum number, 274, 282 probability, diffusion and, 864–866 in quantum mechanics, 281 problem-solving strategies, 42 Problem Solving Tip, aqueous solutions of salts, 771 balanced equations and equilibrium constants, 739 balancing equations in basic solution, 904 balancing oxidation–reduction equations, 903 buffer solutions, 816 calculating ∆T, 215 common entropy-favored processes, 870 concepts of thermodynamics, 860 determining ionic compounds, 77 determining strong and weak acids, 765 drawing Lewis electron dot structures, 355 drawing structural formulas, 447 electrochemical conventions for voltaic cells and electrolysis cells, 930 finding empirical and molecular formulas, 90 formulas for ions and ionic compounds, 76 ligand field theory, 1046 pH during acid–base reaction, 826 pH of equal molar amounts of acid and base, 783 preparing a solution by dilution, 177 reactions with a limiting reactant, 165 recognizing gas-forming reactions, 137 relating rate equations and reaction mechanisms, 705 resonance structures, 362 stoichiometry calculations involving solutions, 181 stoichiometry calculations, 159 using a calculator, 35 using Hess's law, 233 using the quadratic formula, 736 writing net ionic equations, 126 procaine, 801 procaine hydrochloride, 47 product(s)  A substance formed in a chemical reaction, 16, 111 effect of adding or removing, 741 in equilibrium constant expression, 723 heat as, 744 rate of concentration change, 671 product-favored reaction(s)  A reaction in which reactants are completely or largely converted to products at equilibrium, 118 equilibrium constant for, 726 predicting, 876 Project Stardust, 664 proline, structure of, 492 propane, as fuel, 245 combustion of, balanced equation for, 115 enthalpy of combustion, 225 percent composition of, 86 structure of, 440 1,2,3-propanetriol, 459t, 460 propanoic acid, as weak acid, 767 1-propanol, 459t 2-propanol, 459t structure of, 386 propene, 449, 682 hydrogenation of, 385 reaction with bromine, 453 structure of, 429 propionic acid, 468t proportionality constant, 512, 529 proportionality symbol, 676 propyl alcohol, 459t propyl ethyl ether, structure of, 581 propyl propanoate, 472 propylene, 449 protein(s)  A polymer formed by condensation of amino acids, sometimes conjugated with other groups, 491–496 energy content of, 29 as hydrophilic colloids, 645 synthesis, DNA and, 498 testing food for, 565 proton(s)  A positively charged subatomic particle found in the nucleus, 51 bombardment with, 1075 demonstration of, 341 donation by Brønsted acid, 130, 757 name of, 337 nuclear stability and, 1065 proton exchange membrane (PEM), 912 Prout, William, 337 Prussian blue, 1018, 1019 purification, of mixtures, 10 of water, 954 11/22/10 11:30 AM putrescine, 463 Pyrex glass, 661 pyridine, reaction with cisplatin, 202 resonance structures of, 488 structure of, 795 substitutions on, 802 pyrite, iron, 12 pyrolusite, 1011 pyrometallurgy  Recovery of metals from their ores by high-temperature processes, 1023 pyrophosphate ion, manganese(III) ion and, 922 pyrophosphoric acid, 996t pyroxenes, structure of, 986 pyruvate, production of lactate from, 892 quadratic equations, A-4 quadratic formula, use in concentration problems, 734 inde x / g los sa ry radius, atomic, 315 covalent, 317 ionic, 322, 605, 625 radon, from decay of uranium, 1062 radioactive half-life of, 688, 1072 Ramsay, Sir William, 109, 746 Raoult’s law  The vapor pressure of the solvent is proportional to the mole fraction of the solvent in a solution, 630 rare earth elements See lanthanides rare gas(es) See noble gas(es) Raschig reaction, 703, 990 rate See reaction rate(s) rate constant (k)  The proportionality constant in the rate equation, 676, 677 Arrhenius equation for, 693 half-life and, 686 for radioactivity, 1072 units of, 677, 678 qualitative information  Nonnumerical experimental observations, such as descriptive or comparative data, 3, 25 rate equation(s)  The mathematical relationship between reactant concentration and reaction rate, 676 quantitative analysis, 167 determining, 678 for elementary step, 699 first-order, nuclear, 1071 graphical determination of, 684 integrated, 681–689 for nuclear decay, 1072 reaction mechanisms and, 700–706 rate law See rate equation(s) quantitative information  Numerical experimental data, such as measurements of changes in mass or volume, 3, 25 quantity, of pure substance, 80 quantization, 342 of electron spin, 288 of electron’s potential energy, 274, 281 of energy in macroscopic system, 865 of nuclear spin, 291 Planck’s assumption of, 270 quantum dots, 999 quantum mechanics  A general theoretical approach to atomic behavior that describes the electron in an atom as a matter wave, 281–284 quantum number(s)  A set of numbers with integer values that define the properties of an atomic orbital, 281 allowed values of, 282 angular momentum, 282 in macroscopic system, 865 magnetic, 283 Pauli exclusion principle and, 301 principal, 274, 282 spin, 288 quartz, 985 structure of, 601 quaternary structure, of protein, 494 quenching, in steel production, 592 quinine, 101 rad  A unit of radiation dosage, 1081 radial distribution plot, 284 radiation, background, 1081 cancer treatment with, 1085 cosmic, 1081 electromagnetic, 267–269 health effects of, 1081–1083 safe exposure, 1083 treatment of food with, 1086 units of, 1081 radiation absorbed dose (rad), 1081 radioactive decay series  A series of nuclear reactions by which a radioactive isotope decays to form a stable isotope, 1061–1064 radioactivity, discovery of, 338 natural, 1059 radiocarbon dating, 1073 radium, 338 abundance of, 974 from decay of uranium, 1062 kotz_48288_25_Index_I01-I30.indd 23 rate-determining step  The slowest elementary step of a reaction mechanism, 700 reactant(s)  A starting substance in a chemical reaction, 16, 111 concentration of, reaction rate and, 675–681 effect of adding or removing, 741 in equilibrium constant expression, 723 heat as, 744 rate of concentration change, 671 reactant-favored reaction(s)  A reaction in which only a small amount of reactants is converted to products at equilibrium, 118 equilibrium constant for, 726, 727 predicting, 876 reaction(s)  A process in which substances are changed into other substances by rearrangement, combination, or separation of atoms, 16 See also under element, compound, or chemical group of interest acid–base See acid–base reaction(s) addition, 452 in aqueous solution, 119 stoichiometry of, 181–188 types of, 144 autoionization, 761 chain, 1078 condensation, 477 coupling of, 881 direction of, acid–base strength and, 771 reaction quotient and, 727 disproportionation, 1005 electron transfer, 894–945 See also oxidation– reduction reaction(s) enthalpy change for, 224–226 enzyme-catalyzed cleavage, 495 esterification, 469 exchange, 123, 144 free energy change for, 875 Friedel–Crafts, 794 gas laws and, 522–524 gas-forming, 136­­–137, 145 hydrogenation, 385 hydrolysis, 469 I-23 moles of, 165, 224 (n, γ), 1077 neutralization, 133, 774 neutron capture, 1077 nuclear, 1060–1064 artificial, 1075–1078 rates of, 1071–1075 order of See reaction order oxidation of alcohols, 465 oxidation–reduction See oxidation–reduction reaction(s) in petroleum refining, 458 precipitation, 123–128, 144, 828–838 solubility product constant and, 839–843 product-favored vs reactant-favored, 118, 236–238, 726, 859 predicting, 876 rate of See reaction rate(s) reduction of aldehydes and ketones, 466, 469 reduction of carboxylic acids, 468 reductive carbonylation, 1048 reverse, equilibrium constant expression for, 738 reversibility of, 116, 721 spontaneity of, predicting, 872, 875 standard enthalpy of, 224 standard reduction potentials of, 915, 917t substitution, 203, 456 sum of, equilibrium constant expression for, 739 thermite, 142, 156, 164 trans-esterification, 263, 489 water gas, 261, 968 reaction coordinate diagram, 691–692 reaction intermediate  A species that is produced in one step of a reaction mechanism and completely consumed in a later step, 696 in rate law, 704 reaction mechanism(s)  The sequence of events at the molecular level that controls the speed and outcome of a reaction, 669, 697–706 effect of catalyst on, 696 rate equation and, 700–706 rate-determining step of, 700 verification of, 719 reaction order  The exponent of a concentration term in the reaction’s rate equation, 676 determining, 678 molecularity and, 699 reaction quotient (Q)  The product of concentrations of products divided by the product of concentrations of reactants, each raised to the power of its stoichiometric coefficient in the chemical equation, 727–729 See also equilibrium constant Gibbs free energy change and, 876 relation to cell potential, 921 solubility product constant and, 839 reaction rate(s)  The change in concentration of a reagent per unit time, 669–673 Arrhenius equation and, 693 average vs instantaneous, 672 catalysts and, 695–697 collision theory of, 689–693 conditions affecting, 674 effect of temperature, 690 expression for See rate equation(s) initial, 678 radioactive disintegration, 1071–1075 stoichiometry and, 671, 672 receptor proteins, 503 rechargeable battery, 909 recipe, stoichiometry and, 158 11/22/10 11:30 AM I-24 i n d e x /glossary redox reaction(s) See oxidation–reduction reaction(s) reducing agent(s)  The substance that donates electrons and is oxidized in an oxidation–reduction reaction, 138, 896 relative strengths of, 915, 916, 919 reduction  The gain of electrons by an atom, ion, or molecule, 137 of transition metals, 1019 reduction potential(s), standard, 915, 917t standard, values of, A-32 reduction reaction(s), of aldehydes and ketones, 466, 469 of carboxylic acids, 468 reductive carbonylation reaction, 1048 reflection, total internal, 662 reformation, in petroleum refining, 458 refraction, index of, 661 refractories, 663 relative atomic mass See atomic weight rem  A unit of radiation dosage to biological tissue, 1081 renewable energy resources, 257 replication, of DNA, 497 resin, in ion exchanger, 978 resonance, molecular orbital theory and, 424 resonance stabilization, 456 resonance structure(s)  The possible structures of a molecule for which more than one Lewis structure can be written, differing by the number of bond pairs between a given pair of atoms, 356–360 amides, 471 benzene, 356, 415, 454 carbonate ion, 357 effect on acid strength, 789 nitrate ion, 357 nitrite ion, 358 ozone, 356 respiration, 505 production of ATP by, 881 retroviruses, 500 reverse osmosis  The application of pressure greater than the osmotic pressure of impure solvent to force solvent through a semipermeable membrane to the region of lower solute concentration, 637, 955 water purification by, 616 reverse transcriptase, 501 reversibility, equilibrium and, 721 of chemical reactions, 116 reversible process  A process for which it is possible to return to the starting conditions along the same path without altering the surroundings, 862 Rhazes (Abu Bakr Mohammad ibn Zakariyya al-Razi), 335 rhodium, 327 rhodochrosite, 150, 829, 831 rhubarb, oxalic acid in, 806 ribonucleic acid, 496 hydrogen bonding in, 561 ribose, 496 ribosome, 498 ring structure, in benzene, 415 RNA See ribonucleic acid RNA World hypothesis, 499–500 roasting, of copper ore, 202 of metal sulfides, 195 Roberts, Ainé, 518 rock salt structure, 593 roentgen  A unit of radiation dosage, 1081 Roentgen, Wilhelm, 1081 Roman numerals, in names of cations, 74, 75 kotz_48288_25_Index_I01-I30.indd 24 root-mean-square (rms) speed  The square root of the average of the squares of the speeds of the molecules in a sample, 530 roots, calculating with logarithms, A-4 on calculator, 35 rose petals, pigment as indicator, 826 Rosenberg, Barnett, 1047 rotation, A-6 around bonds in alkanes, 445 of polarized light, 441, 442 around sigma and pi bonds, 415, 441 rounding off, 37 Rowland, Sherwood, 951 ROY G BIV, 1043 rubber, isoprene in, 476 natural and synthetic, 476 styrene-butadiene, 476 vulcanized, 476 rubidium, abundance of, 969 radiochemical dating with, 1091, 1094 ruby, 300 ion charges in, 73 synthetic, 983 rust, 1021 See also iron(III) oxide Rutherford, Ernest, 51, 337, 339, 1059, 1075 rutile, in rubies, 300 unit cell of, 609 Rydberg, Johannes, 272 Rydberg constant, 273 s-block elements, 307 s orbital(s) See atomic orbital(s) saccharin, 201 structure of, 105, 454, 801 sacrificial anode, 945 safety match, 995, 1005 salad dressing, as emulsion, 645 salicylic acid, 166, 470, 756 structure of, 855 salt(s)  An ionic compound whose cation comes from a base and whose anion comes from an acid, 132–136 acid–base properties of, 769–771 calculating pH of aqueous solution, 781 concentration in sea water, 187 electrolysis of, 929 hydrated, 553 insoluble, precipitation of, 839–843 solubility of, 828–838 solubility product constants of, 830t salt bridge  A device for maintaining the balance of ion charges in the compartments of an electrochemical cell, 903 saltpeter, 251, 970, 973 salvarsan, in syphilis treatment, 92 samarium, 327, 333 sandwich compounds, 1049 sapa, 988 sapphire, 300, 983 sarin, 784 saturated compound(s)  A hydrocarbon containing only single bonds, 444 See also alkanes saturated solution(s)  A stable solution in which the maximum amount of solute has been dissolved, 620, 829 reaction quotient in, 839 scanning electron microscopy (SEM), 27 Scheele, Carl Wilhelm, 112, 1002, 1011 Schrödinger, Erwin, 281, 342 science, goals of, methods of, 2–5 scientific notation, 33–35, A-2 operations in, 34 Scott, Robert, 615 Scott Couper, Archibald, 338 screening, of nuclear charge, 304 scrubber, flue gas, 536 for coal-fired power plant, 258 SCUBA diving, gas laws and, 534 Henry’s law and, 626 sea level, rising, 953 sea urchin, 17 calcium carbonate in, 660 sea water, density of, 39 halogens in, 1001 ion concentrations in, 653t, 954t magnesium in, 975 pH of, 180 reverse osmosis of, 637 salt concentration in, 187 sodium and potassium ions in, 970 Seaborg, Glenn T., 1075 second, definition of, A-10 second-order reaction, 676 half-life of, 686 integrated rate equation, 683 second law of thermodynamics  The total entropy of the universe is continually increasing, 861 secondary alcohols, 465 secondary battery, 909 secondary colors, 1043 secondary structure, of protein, 493, 494 seesaw molecular geometry, 368, 369 selenium, abundance of, 998 uses of, 998, 999 semiconductor(s)  Substances that can conduct small quantities of electric current, 596–598 applications of, 659 band theory of, 596 semimetals See metalloid(s) semipermeable membrane  A thin sheet of material through which only certain types of molecules can pass, 635 sequestration, geological, of carbon dioxide, 536 serial dilution, 178 serine, structure of, 492 setae, on geckos’ toes, 548 shielding constant, effective nuclear charge and, 332 SI  Abbreviation for Système International d’Unités, a uniform system of measurement units in which a single base unit is used for each measured physical quantity, 25, A-10 sickle cell anemia, 494 siderite, 150 sievert  The SI unit of radiation dosage to biological tissue, 1081 sigma (𝛔) bond(s)  A bond formed by the overlap of orbitals head to head, and with bonding electron density concentrated along the axis of the bond, 403 sign conventions, for electron affinity, 320 for energy calculations, 221t for voltaic cells, 905 significant figure(s)  The digits in a measured quantity that are known exactly, plus one digit that is inexact to the extent of ±1, 35–38 in atomic masses, 81 in calculating empirical formulas, 90 logarithms and, A-3 silane, comparison to methane, 960 reaction with oxygen, 540 silica, 985 silica aerogel, 663 silica gel, 986 11/22/10 11:30 AM silicates, minerals containing, 986 structure of, 601 silicon, abundance of, 984 bond energy compared to carbon, 442 chemistry of, 984–988 compounds of, 64 purification of, 984 reaction with methyl chloride, 541 as semiconductor, 597 similarity to boron, 977 similarity to carbon, 960 structure of, 584 unit cell of, 613 silicon carbide, 1010 structure of, 594 unit cell of, 612 silicon dioxide, 985 comparison to carbon dioxide, 960 in glass, 661 reaction with hydrogen fluoride, 1004 silicon tetrachloride, 984 molecular geometry of, 365 silicone polymers, 987–988 waterproofing with, 201 Silly Putty, 988 silt, formation of, 645 silver, as bacteriocide, 144 density of, 45, 48 isotopes of, 98 sterling, 658 silver acetate, solubility of, 834 silver bromide, reaction with sodium thiosulfate, 198 solubility of, 829 in aqueous thiosulfate ion, 846 silver chloride, free energy change of dissolution, 883 Ksp of, 928 precipitation of, 124, 126 solubility of, 833, 835, 840 in aqueous ammonia, 738, 844 silver chromate, 187 formation by precipitation, 125 solubility of, 834, 836 silver coulometer, 943 silver nitrate, reaction with potassium chloride, 124, 126 silver oxide, decomposition of, 890 silver oxide battery, 910 silver sulfide, reaction with aluminum, 153 silver-zinc battery, 942 simple cubic (sc) unit cell, 585 single bond  A bond formed by sharing one pair of electrons; a sigma bond, 403 slag, in blast furnace, 1025 slaked lime, 135, 954 Slater's rules, 332 slime, 476 slope, of straight line graph, 41, 684 Smalley, Richard, 255 smog, 261 photochemical, 949 snot-tites, 1001 soap  A salt produced by the hydrolysis of a fat or oil by a strong base, 645 hard water and, 978 soapstone, 974 soda ash, 972, 973 See sodium carbonate soda-lime glass, 661 soda-lime process, 972 Soddy, Frederick, 340, 1060 kotz_48288_25_Index_I01-I30.indd 25 inde x / g los sa ry sodium, abundance of, 969 in fireworks, 279 preparation of, 970 reaction with chlorine, 3, 141, 345, 346 reaction with water, sodium acetate, calculating pH of aqueous solution, 781 in heat pack, 622 sodium azide, 522 in air bags, 509, 516, 540 preparation of, 200 production of, 545 sodium benzoate, 88 sodium bicarbonate, 972 See also sodium hydrogen carbonate reaction with acetic acid, 773 sodium borohydride, 982, 1012 as reducing catalyst, 466 sodium carbonate, 175 calculating pH of aqueous solution, 785 industrial uses, 972 primary standard for acid–base titration, 185 sodium chloride, as strong electrolyte, 119 composition of, 3, 12 crystal lattice of, 77 electrolysis of, 522, 930, 970 entropy of solution process, 871 ion charges in, 73 lattice enthalpy calculation for, 600 melting ice and, 640 oxidation by dichromate ion, 1002 reaction with sulfuric acid, 1004 standard enthalpy of formation of, 233 structure of, 584, 591 sodium cyanide, extraction of gold with, 857 sodium fluoride, 47 sodium glycinate, 363 sodium halides, products of electrolysis of, 933 sodium hydrogen carbonate, reaction with citric acid, 144 reaction with tartaric acid, 136 sodium hydrosulfite, preparation of, 201 sodium hydroxide, commercial preparation of, 972 enthalpy of solution, 623 production of, 1002 reaction with acetic acid, 133 reaction with aluminum, 968, 969 reaction with formic acid, 774 reaction with hydrogen chloride, 132 reaction with methyl acetate, 678 titration of acetic acid, 820, 822 titration with hydrochloric acid, 818 sodium hypochlorite, 189 in bleach, 619 as disinfectant, 954 reaction with ammonia, 990 sodium iodide, aqueous, electrolysis of, 931 reaction with thallium(I) sulfate, 197 sodium ions, in ion exchanger, 978 pumping in cells, 505 sodium laurylbenzenesulfonate, structure of, 646 sodium monohydrogen phosphate, 997 sodium nitrate, reaction with sulfuric acid, 993, 994 sodium nitrite, reaction with sulfamic acid, 544 sodium perchlorate, 1005 sodium peroxide, 971 sodium pertechnetate, 298 sodium phosphate, 997 sodium polyacrylate, in disposable diapers, 481 sodium silicate, 985 I-25 sodium stearate, as soap, 645 sodium sulfate, quantitative analysis of, 167 reaction with barium chloride, 127 sodium sulfide, preparation of, 196 sodium sulfite, 1009 sodium thiosulfate, reaction with iodine, 189 reaction with silver bromide, 198 titration with iodine, 202 sol  A colloidal dispersion of a solid substance in a fluid medium, 644t solar cell, 659 solar energy, 265 solar panel, 20 solid(s)  The phase of matter in which a substance has both definite shape and definite volume, amorphous, 601 chemistry of, 582–615 compressibility of, 550 concentration of, in equilibrium constant expression, 724 dissolution in liquids, 622 ionic, 590–594 molecular, 601 network, 601 types of, 583t Solomon, Susan, 951 solubility  The concentration of solute in equilibrium with undissolved solute in a saturated solution, 620 common ion effect and, 834–836 of complex ions, 843–846 estimating from solubility product constant, 830–834 factors affecting, 626–628 of gases in water, 560t intermolecular forces and, 553 of ionic compounds in water, 122 of salts, 828–838 undissociated salt and, 833 solubility product constant (Ksp)  An equilibrium constant relating the concentrations of the ionization products of a dissolved substance, 829 isotopic measurement of, 1086 reaction quotient and, 839 standard potential and, 927, 928t values of, A-23 solute  The substance dissolved in a solvent to form a solution, 119, 617 solution(s)  A homogeneous mixture in a single phase, 8–10, 616–655 acidic and basic, redox reactions in, 899–902 alloy as, 658 aqueous, balancing redox equations, 899–902 pH and pOH of, 178–180, 763 reactions in, 119 boiling process in, 632 buffer See buffer solution(s) concentrations in, 173–177 enthalpy of, 623–626 ideal, 630 osmosis in, 635 process of forming, 620–626 Raoult’s law, 630 saturated, 620 solvation, effect on acid strength, 788 enthalpy of, 551 Solvay process, 972, 1047 solvent  The medium in which a solute is dissolved to form a solution, 119, 617 soy, adhesive based on, 481 space-filling models, 68, 441 spatulae, on geckos’ toes, 548 11/22/10 11:30 AM I-26 i n d e x /glossary spdf notation  A notation for the electron configuration of an atom in which the number of electrons assigned to a subshell is shown as a superscript after the subshell’s symbol, 283, 307 specific heat, values of, A-14t specific heat capacity (C)  The quantity of heat required to raise the temperature of 1.00 g of a substance by 1.00 kelvin, 212 determining, 214 hydrogen bonding and, 559 spectator ion(s)  An ion that is present in a solution in which a reaction takes place but that is not involved in the net process, 126 spectrochemical series  An ordering of ligands by the magnitudes of the splitting energies they cause, 1044–1046 spectrometer, mass, 54, 55 spectrophotometer, 49 spectrophotometry  An analytical method based on the absorption and transmission of specific wavelengths of light, 188–193 spectroscope, 337 photoelectron, 437 spectrum, absorption, 188, 1044 electromagnetic, 269, 1043 continuous, 272 of heated body, 269, 270 line, 272, 273 solar, 299 speed(s), of gas molecules, 529 of wave, 267 spinel(s), 330 structure of, 612 sponge, skeletal structure of, 27, 663 spontaneous reaction, 859 See also productfavored reaction(s) effect of temperature on, 873 Gibbs free energy change and, 875–877 relation to enthalpy and entropy, 872t square-planar molecular geometry, 368, 369, 1034 square-pyramidal molecular geometry, 368, 369 stability, band of, 1065 of organic compounds, 442 standard enthalpy of formation and, 234 stabilization, resonance, 456 stainless steel, 1025 stalactites and stalagmites, 116 standard atmosphere (atm)  A unit of pressure; atm = 760 mm Hg, 510, A-7t standard conditions  In an electrochemical cell, all reactants and products are pure liquids or solids, or 1.0 M aqueous solutions, or gases at a pressure of bar, 913 standard deviation  A measure of precision, calculated as the square root of the sum of the squares of the deviations for each measurement from the average divided by one less than the number of measurements, 32 standard free energy change of reaction (∆rG°)  The free energy change for a reaction in which all reactants and products are in their standard states, 874 standard hydrogen electrode (SHE), 914 standard molar enthalpy of formation (∆f H°)  The enthalpy change of a reaction for the formation of one mole of a compound directly from its elements, all in their standard states, 233, 860 enthalpy of solution calculated from, 625 values of, A-26 standard molar enthalpy of fusion (∆fusH°)  The quantity of energy as heat required to convert mol of a solid to a liquid at bar and constant temperature, 225 kotz_48288_25_Index_I01-I30.indd 26 standard molar enthalpy of vaporization (∆vapH°)  The quantity of energy as heat required to convert mol of a liquid to a gas at bar and constant temperature, 225, 560t, 566 standard molar entropy (S°)  The entropy of a substance in its most stable form at a pressure of bar, 866 values of, A-26 standard molar free energy of formation  (∆f G°) The free energy change for the formation of one  mole of a compound from its elements, all in their standard states, 878 values of, A-26 standard molar volume  The volume occupied by mol of gas at standard temperature and pressure; 22.414  L, 519 standard potential (E °cell)  The potential of an electrochemical cell measured under standard conditions, 913 of alkali metals, 972 calculation of, 915, 918 equilibrium constant calculated from, 926 standard reaction enthalpy (∆rH°)  The enthalpy change of a reaction that occurs with all reactants and products in their standard states, 224 product-favored vs reactant-favored reactions and, 236–238 standard reduction potential(s), 915, 917t of halogens, 1002t values of, A-32 standard state  The most stable form of an element or compound in the physical state in which it exists at bar and the specified temperature, 224, 860 standard temperature and pressure (STP)  A temperature of °C and a pressure of exactly atm, 519 standardization  The accurate determination of the concentration of an acid, base, or other reagent for use in a titration, 184 standing wave  A single-frequency wave having fixed points of zero amplitude, 281 starch, 467 starch-iodide paper, 189 stars, elements formed in, 51 state(s), changes of, 216 ground and excited, 274 physical, of matter, 7, 549 reaction enthalpy and, 225 standard See standard state state function  A quantity whose value is determined only by the state of the system, 222, 860 stationary phase, in chromatography, 581 steam reforming, 263, 265 stearic acid, 468t, 489 steel, high-strength, 592 production of, 1025 stereoisomers  Two or more compounds with the same molecular formula and the same atom-toatom bonding but with different arrangements of the atoms in space, 440 sterilization, 954 by irradiation, 1086 sterling silver, 658 Stern, Otto, 288 steroids, 502 stibnite, 106, 831 stoichiometric coefficients  The multiplying numbers assigned to the species in a chemical equation in order to balance the equation, 113 electrochemical cell potential and, 918 exponents in rate equation vs., 676 fractional, 225 in calculating enthalpy of formation, 234 in equilibrium constant expression, 723 stoichiometric factor(s)  A conversion factor relating moles of one species in a reaction to moles of another species in the same reaction, 158, 523 in solution stoichiometry, 181 in titrations, 184 stoichiometry  The study of the quantitative relations between amounts of reactants and products, 113 ICE table and, 723 ideal gas law and, 522–524 mass relationships in, 157–160 rate equation of elementary step and, 699 reaction rates and, 671, 672 of reactions in aqueous solution, 181–188 unit cell and, 584 storage battery, 909 STP See standard temperature and pressure strained hydrocarbons, 448 Strassman, Fritz, 1078 strategies, problem-solving, 42 stratosphere, 528, 948 strong acid(s)  An acid that ionizes completely in aqueous solution, 129, 764 reaction with strong base, 774 reaction with weak base, 775 titration of, 818–820 strong base(s)  A base that ionizes completely in aqueous solution, 129, 764 strong electrolyte  A substance that dissolves in water to form a good conductor of electricity, 119, 120 strontium, 327 abundance of, 974 in fireworks, 279 in meteorite dating, 1094 isotopes of, 98 ratios, 58 strontium carbonate, enthalpy of formation, 246 strontium sulfate, 852 structural formula  A variation of a molecular formula that expresses how the atoms in a compound are connected, 67, 441, 447 structural isomers  Two or more compounds with the same molecular formula but with different atoms bonded to each other, 440, 1034 of alcohols, 459, 460 of alkanes, 444 of alkenes, 449 boiling points of, 580 structure, molecular, 345 Strutt, John William (Lord Rayleigh), 109 styrene, enthalpy of formation, 244 in ABS plastic, 478 structure of, 455 styrene-butadiene rubber (SBR), 476 Styrofoam, 475t Styron, 475t subatomic particles  A collective term for protons, neutrons, and electrons, 51 properties of, 53t sublimation  The direct conversion of a solid to a gas, 219, 605 pressure–volume work in, 250 submicroscopic level  Representations of chemical phenomena in terms of atoms and molecules; also called particulate level, entropy at, 862–864 subshells, labels for, 283 number of electrons in, 302t order of energies of, 303 substance(s), pure  A form of matter that cannot be separated into two different species by any physical technique and that has a unique set of properties, amount of, 80 11/22/10 11:30 AM substituent groups, common, A-16t substitution reaction(s), 203 of aromatic compounds, 456 substitutional alloy, 658 substrate, in enzyme-catalyzed reaction, 495, 702 successive approximations, method of, 735, 779 successive equilibria, 843 succinic acid, reaction with 1,2-ethylenediamine, 480 sucrose, as nonelectrolyte, 121 enthalpy of combustion, 225 half-life of decomposition, 687 hydrolysis of, 710 rate of decomposition of, 673 structure of, 467 sugar, dietary Calories in, 225 reaction with silver ion, 153 sulfamate ion, structure of, 433 sulfamic acid, reaction with sodium nitrite, 544 sulfanilic acid, structure of, 803 sulfate ion, orbital hybridization in, 411 resonance structures of, 359 structure of, 353t sulfide(s), in black smokers, 110 roasting of, 999 sulfonate group, in detergents, 646 sulfur, abundance of, 998 allotropes of, 65, 998, 999 chemistry of, 999 in coal, 258 combustion of, 242, 724 compounds with phosphorus, 995 density of, 23 in iron pyrite, 12 mining of, 133 natural deposits of, 998 phase transition of, 889 reaction with oxygen, 114 sulfur dioxide, 1000 electrostatic potential map of, 395 as Lewis acid, 794 reaction with calcium carbonate, 889 reaction with oxygen, 730 reaction with water, 135 as refrigerant, 951 scrubbing from flue gas, 536 sulfur hexafluoride, 361 molecular orbitals in, 427 preparation of, 196 sulfur tetrafluoride, molecular polarity of, 379 orbital hybridization in, 411 sulfur trioxide, 1000 decomposition of, 889 enthalpy of formation, 243 structure of, 433 sulfuric acid, 1000 dilution of, 204 heat of dissolution in water, 241 in lead storage battery, 910 as polyprotic acid, 759 production of, 1009 production of, from elemental sulfur, 1001 properties and uses of, 133 reaction with hydrazine, 198 reaction with nickel(II) carbonate, 137 reaction with sodium chloride, 1004 reaction with sodium nitrate, 993, 994 reaction with water, 130 structure of, 99, 353t sulfuryl chloride, decomposition of, 710, 752 kotz_48288_25_Index_I01-I30.indd 27 inde x / g los sa ry Sullivan, John H., 719 sun, chemistry of, 299 sunscreens, 272 superacid(s), 805 superconductivity, 665 superconductor(s)  A material that has no resistance to the flow of electric current, 155, 256 supercritical fluid  A substance at or above the critical temperature and pressure, 571, 607 superoxide ion, 430 molecular orbital configuration of, 422 superoxides, 971 oxidation number of oxygen in, 140 superphosphate fertilizer, 151, 1000 supersaturated solution(s)  A solution that temporarily contains more than the saturation amount of solute, 622 reaction quotient in, 839 surface area, of colloid, 643 reaction rate and, 675 surface density plot, 284, 285 surface tension  The energy required to disrupt the surface of a liquid, 571–573 detergents and, 645 surfactant(s)  A substance that changes the properties of a surface, typically in a colloidal suspension, 645–646 supercritical carbon dioxide and, 574 surroundings  Everything outside the system in a thermodynamic process, 210, 860 entropy change for, 870 sustainability, 5–6 swamp gas, 259 sweat, cooling by, 568 symbol(s), in chemistry, 8, 10–11 ionic charge in, 70 symmetry, chirality and, 441, 446 molecular polarity and, 379 synthesis gas, 968 system  The substance being evaluated for energy content in a thermodynamic process, 210, 860 entropy change for, 870 systematic names, 447, A-15 Système International d’Unités, 25, A-10 T-shaped molecular geometry, 368, 369 talc, 974 TAML, 1057 tantalum, 327 tar sands, 259 tarnish, on silver, 153 tartaric acid, 468t as polyprotic acid, 759 reaction with sodium hydrogen carbonate, 136 titration of, 199 technetium, 298, 1078 technetium-99m, 1084 Teflon, 475t density of, 22 tellurium, abundance of, 998 temperature  A physical property that determines the direction of heat flow in an object on contact with another object, 211 of atmosphere, 948 change in, heat and, 212 in collision theory, 690, 692 constant during phase change, 216 critical, 571 effect on solubility, 627 effect on spontaneity of processes, 873 electromagnetic radiation emission and, 269, 270 I-27 energy and, 211 equilibrium constant and, 744 equilibrium vapor pressure and, 569 free energy and, 880–882 gas, volume and, 514 ionization constant for water and, 761t molecular speed and, 530 physical properties and, 13, 14 reaction rate and, 674 scales for measuring, 25–27 standard, 519 superconductivity and, 155 tempering, of steel, 1025 terbium oxide, 154 terephthalic acid, structure of, 478 termolecular process, 698 tertiary alcohols, 465 tertiary structure, of protein, 493, 494 tetraamido-macrocyclic ligand (TAML), 1057 tetracarbonyl nickel, 1047 tetrachloromethane See carbon tetrachloride tetraethyl lead, combustion of, balanced equation for, 115 tetrafluoroethylene, dimerization of, 713 effusion of, 533 tetragonal unit cell, 585 tetrahedral electron-pair geometry, orbital hybridization and, 405, 406 tetrahedral holes, 591 tetrahedral molecular geometry, 365, 1034 in carbon compounds, 439, 440 in DNA backbone, 388 3,5,39,59-tetraiodothyronine,structure of, 1087 thallium, abundance of, 979 isotopes of, 98 thallium(I) sulfate, reaction with sodium iodide, 197 Thenard, Louis, 167 thenardite, 167 theobromine, structure of, 438 theoretical plate(s), 655 theoretical yield  The maximum amount of product that can be obtained from the given amounts of reactants in a chemical reaction, 165 theory  A unifying principle that explains a body of facts and the laws based on them, atomic See atomic theory of matter kinetic-molecular, 7, 527–531, 549 molecular orbital See molecular orbital theory quantum See quantum mechanics valence bond See valence bond theory VSEPR See valence shell electron pair repulsion (VSEPR) model thermal energy  The energy due to the motion of atoms, molecules, or ions, 16 thermal equilibrium  A condition in which the system and its surroundings are at the same temperature, 210 thermite reaction, 142, 156, 164 thermodynamics  The study of energy conversion as heat or work, 209, 860 first law of, 219–223, 860 second law of, 861 third law of, 866 thermoplastic polymer(s)  A polymer that softens but is unaltered on heating, 473 thermosetting polymer(s)  A polymer that degrades or decomposes on heating, 473 thermosphere, 528 Thiobacillus ferrooxidans, 1025 thiocyanate ion, linkage isomers containing, 1035 thionyl chloride, 332 11/22/10 11:30 AM I-28 i n d e x /glossary thioridazine, 204 third law of thermodynamics  The entropy of a pure, perfectly formed crystal at K is zero, 866 Thompson, Benjamin (Count Rumford), 211 Thomson, Sir Joseph John, 51, 338 Thomson, William See Kelvin, Lord thorium, radioactive decay of, 340 three-center bond, 427, 982 threonine, structure of, 492 thymine, 388 hydrogen bonding to adenine, 498, 561 structure of, 344 thyroid gland, imaging of, 1084 treatment of hyperthyroidism, 1087 thyroxine, 1002, 1087 tin, 327 abundance of, 984 allotropes of, 615 density of, 45 tin disease, 615 tin(II) chloride, aqueous, electrolysis of, 932 tin(IV) iodide, formula of, 90 tin(IV) oxide, 1013 titanium, density of, 45 in memory metal, 1016 uses of, 1022 titanium(IV) chloride, reaction with water, 200 synthesis of, 151 titanium(IV) ion, in sapphire, 300 titanium(IV) oxide, 988, 1000 as pigment, 1018 quantitative analysis of, 169 reaction with carbon, 890 in rubies, 300 titrant  The substance being added during a titration, 820 titration  A procedure for quantitative analysis of a substance by an essentially complete reaction in solution with a measured quantity of a reagent of known concentration, 182–184 acid–base, 182, 818–828 curves for, 818, 820, 821 oxidation–reduction, 186 Tollen's test, 153 toluene, structure of, 397, 454 ton, metric, 948 tonicity, 640 torr  A unit of pressure equivalent to one millimeter of mercury, 510, A-7t Torricelli, Evangelista, 510 total internal reflection, 662 tracer, radioactive, 1085 transcriptase, reverse, 501 transcription, error rates of, 501 of DNA, 498 trans-dichlorobis(ethylenediamine)cobalt(III) ion, 716 trans-esterification reaction, 489 transfer RNA (tRNA), 499 transistor, 659 transition, d-to-d, 1044 transition elements  Some elements that lie in rows to of the periodic table, comprising scandium through zinc, yttrium through cadmium, and lanthanum through mercury, 60, 61, 66, 310, 314 atomic radii, 317, 318 cations formed by, 71 chemistry of, 1016–1056 commercial production of, 1023–1026 electron configurations of, 1019 naming in ionic compounds, 75 kotz_48288_25_Index_I01-I30.indd 28 oxidation numbers of, 1019, 1020 properties of, 1018–1023 transition state  The arrangement of reacting molecules and atoms at the point of maximum potential energy, 691 translation, A-6 of RNA, 499 transmittance (T)  The ratio of the amount of light transmitted by the sample to the amount of incident light, 189 transmutation See nuclear reaction(s) transport proteins, 503 transuranium elements, 1076, 1077 trendline, 41 triatomic molecules, of elements, 64 tribromomethane, density of, 23 trichlorobenzene, isomers of, 455 trichloromethane, density of, 23 triclinic unit cell, 585 triglycerides, 501 trigonal-pyramidal molecular geometry, 366 trigonal-bipyramidal electron-pair geometry, orbital hybridization and, 405, 410 trigonal-bipyramidal molecular geometry, 365 axial and equatorial positions in, 368, 369 trigonal-planar electron-pair geometry, in benzene, 416 orbital hybridization and, 405, 408 trigonal-planar molecular geometry, 365 in carbon compounds, 439 in DNA structure, 389 trigonal-pyramidal molecular geometry, orbital hybridization and, 405 triiodide ion, orbital hybridization in, 411 trimethylamine, structure of, 795 trimethylborane, dissociation of, 753 triphenylmethyl radical, 755 triple bond  A bond formed by sharing three pairs of electrons, one pair in a sigma bond and the other two in pi bonds, 348 valence bond theory of, 414 triple point  The temperature and pressure at which the solid, liquid, and vapor phases of a substance are in equilibrium, 606 tritium, 54, 966, 1091 fusion of, 1080 trona, 972 troposphere, 528, 948 tryptophan, structure of, 492 tube wells, 957 tungsten, melting point of, 1018 unit cell of, 611 tungsten(IV) oxide, reaction with hydrogen, 151 turquoise, 831 density of, 21 Tyndall effect, 643 Tyrian purple dye, 426 tyrosine, structure of, 492 U.S Food and Drug Administration (FDA), 189 ulexite, 979 ultraviolet catastrophe, 269 ultraviolet (UV) radiation, 268 absorption by ozone, 951 disinfection by, 955 in photoelectron spectroscopy, 437 skin damage and, 272 uncertainty principle, 282 unimolecular process, 698 unit(s), of measurement, 25–30, 510 SI, 25, A-10 unit cell(s)  The smallest repeating unit in a crystal lattice, 584 number of atoms in, 586 shapes of, 585 universe, entropy change for, 870 total energy of, 18 unpaired electrons, in transition metal ions, 1019 paramagnetism of, 289 unsaturated compound(s)  A hydrocarbon containing double or triple carbon–carbon bonds, 451 unsaturated solution(s), reaction quotient in, 839 ununseptium, discovery of, 1076 uracil, 497, 561 structure of, 398, 804 uranium, fission reaction of, 1078 isotopes of, 1058 isotopic enrichment, 1079 isotopic separation, 1004 radioactive series from, 1061 uranium-235, fission of, 1079 uranium hexafluoride, 1004, 1020, 1079 synthesis of, 151 uranium(IV) oxide, 107 uranyl(IV) nitrate, 1056 urea, conversion of ammonium cyanate to, 713 production of, 200 structure of, 393 synthesis of, 151 urine, phosphorus distilled from, 993 valence band, 596 valence bond theory  A model of bonding in which a bond arises from the overlap of atomic orbitals on two atoms to give a bonding orbital with electrons localized between the atoms, 401–416 valence electron(s)  The outermost and most reactive electrons of an atom, 307, 345–347 Lewis symbols and, 347 of main group elements, 962 valence shell electron pair repulsion (VSEPR) model  A model for predicting the shapes of molecules in which structural electron pairs are arranged around each atom to minimize electronelectron repulsions, 364 valency, 337 valeric acid, 468t valine, structure of, 492 van Arkel, Anton Eduard, 1015 van Arkel–Ketelaar triangle, 1015 van der Waals, Johannes, 535 van der Waals equation  A mathematical expression that describes the behavior of nonideal gases, 535 van der Waals force(s), 548, 550, 563 van’t Hoff, Jacobus Henrikus, 337, 641 van’t Hoff factor  The ratio of the experimentally measured freezing point depression of a solution to the value calculated from the apparent molality, 641 vanadium, 327 vanillin, structure of, 395 vapor pressure  The pressure of the vapor of a substance in contact with its liquid or solid phase in a sealed container, 568–571 Raoult’s law and, 630 relation to enthalpy of vaporization, 570 of water, A-19 vaporization  The state change from liquid to gas, 216, 565 enthalpy of, 567t, A-14t intermolecular forces and, 552, 554t heat of, 216 11/22/10 11:30 AM Vectra, 475t velocity, of wave, 267 Verneuil, Auguste, 300 vibration, A-6 Villard, Paul, 1060 vinegar, 465 pH of, 178 reaction with baking soda, 773 vinyl alcohol, structure of, 392 structure of, 431 viscosity  The resistance of a liquid to flow, 572 visible light, 268, 1043 vitamin B12, cobalt in, 1018 vitamin C See ascorbic acid volatile organic compounds (VOCs), 574, 953 volatility  The tendency of the molecules of a substance to escape from the liquid phase into the gas phase, 569 volcano, chloride ions emitted by, 187 sulfur emitted by, 998 volt (V)  The electric potential through which coulomb of charge must pass in order to joule of work, 913, A-7, A-11 Volta, Alessandro, 896 voltage, cell potential vs., 915 voltaic cell(s), 896, 903–908 commercial, 908–913 electrodes in, 930t volume, constant, calorimetry at, 228 constant, heat transfer at, 222 effect on gaseous equilibrium of changing, 743, 749 gas, pressure and, 512 temperature and, 514 measurement of, 29 per molecule, 534 physical state changes and, 549 standard molar, 519 volumetric flask, 173, 175 wallboard, gypsum in, 94 Walton, E T S., 1075 washing soda, 972 See also sodium carbonate water, amphiprotic nature of, 131 in atmosphere, 947 autoionization of, 761 balancing redox equations with, 899–902 boiling point elevation and freezing point depression constants of, 633t bond angles in, 366 as Brønsted base, 130 concentration of, in equilibrium constant expression, 724 corrosion and, 1021 critical temperature, 571 density of, temperature and, 13t, 557 diminishing supplies of, 955 as electroactive substance, 931 electrolysis of, 11, 263, 998 electrostatic potential map of, 378 enthalpy of formation, 230 environmental concerns, 953–959 expansion on freezing, formation by acid–base reactions, 132 kotz_48288_25_Index_I01-I30.indd 29 inde x / g los sa ry generated by hydrogen–oxygen fuel cell, 912 as greenhouse gas, 952 hard, 978 heat of fusion, 216 heat of vaporization, 216 heavy, 54 in hydrated compounds, 94 interatomic distances in, 28 iodine solubility in, 562 ionization constant for (Kw), 761 molecular polarity of, 377 orbital hybridization in, 407 pH of, 178 phase diagram of, 606, 607 pollution of, 956–958 purification of, 10, 954 by reverse osmosis, 616 reaction with alkali metals, 62, 969, 970 reaction with aluminum, 901 reaction with hydrides, 968, 969 reaction with insoluble salts, 837 reaction with lithium, 523 reaction with methane, 196 reaction with potassium, 23, 62 reaction with sodium, relation to alcohols, 461 solubility of alcohols in, 461 solubility of gases in, 560t solubility of ionic compounds in, 122, 623, 625 solvent in aqueous solution, 119 specific heat capacity of, 212t, 213, 559 standard molar enthalpy of vaporization of, 567 treatment, methods of, 954 with hydrazine, 990 triple point of, 606 vapor pressure of, A-19 curves for, 569 water gas, 148, 245, 246 water gas reaction, 263, 968 water glass, 985 water softener, 978 Watson, James D., 387, 497, 561 watt  A unit of power, defined as joule/second, A-7 wave, matter as, 278 wave mechanics See quantum mechanics wave-particle duality  The idea that the electron has properties of both a wave and a particle, 278–280 wavefunction(s) (𝛙)  A set of equations that characterize the electron as a matter wave, 281 addition and subtraction of, 418 for hydrogen 1s orbital, 298 phases of, 421 radial and angular components of, 287 wavelength (𝛌)  The distance between successive crests (or troughs) in a wave, 267 choice for spectrophotometric analysis, 191 of moving mass, 278 weak acid(s)  An acid that is only partially ionized in aqueous solution, 129, 764 calculating pH of aqueous solution, 778 in buffer solutions, 811 ionization constants, A-20 I-29 reaction with strong base, 774 reaction with weak base, 775 titration of, 820 weak base(s)  A base that is only partially ionized in aqueous solution, 129, 764 in buffer solutions, 811 calculating pH of aqueous solution, 780 ionization constants, A-22 titration of, 824 weak electrolyte  A substance that dissolves in water to form a poor conductor of electricity, 120, 121 weather, heat of vaporization of water and, 568 weight, mass and, A-6 weight percent, of solution, 619 Wilkins, Maurice, 387, 561 Wilkinson's catalyst, 1056 wintergreen, oil of, 470, 638 wolframite, 1020 work  Energy transfer that occurs as a mass is moved through a distance against an opposing force, 219 in electrochemical cell, 925 energy transferred by, 211 Gibbs free energy and, 877 pressure–volume, 221 sign conventions for, 221t xanthines, 438 xenon, compounds of, 400 xenon difluoride, 400, 361 xenon oxytetrafluoride, molecular geometry of, 370 xenon tetrafluoride, 368, 369 xerography, selenium in, 998 x ray(s), 268 in photoelectron spectroscopy, 437 x-ray crystallography, 387, 588 yeast, acetic acid produced by, 468 yield, of product in a chemical reaction, 165 ytterbium, 327 yttrium, 333 Zeise's salt, 1049 zeolite(s), 987 in ion exchanger, 978 zeroes, as significant figures, 36 zero-order reaction, 676, 677 half-life of, 686 integrated rate equation, 684 zinc, density of, 45, 48 reaction with dioxovanadium(V) ion, 899 reaction with hydrochloric acid, 128, 182, 205 in sacrificial anode, 945 zinc blende, structure of, 591 zinc chloride, in dry cell battery, 909 zinc-oxygen battery, 910 zinc sulfide, structure of, 591 zirconium, 327 zone refining, 984 985 Zosimos, 335 zwitterion  An amino acid in which both the amine group and the carboxyl group are ionized, 492,   803 11/22/10 11:30 AM This page intentionally left blank Physical and Chemical Constants Avogadro’s number Electronic charge Faraday’s constant Gas constant N  e  F  R   6.0221415  1023/mol p 1.60217653  1019 C Planck’s constant 9.6485338  104 C/mol electrons Speed of light 8.314472 J/K  mol   (in a vacuum) 0.082057 L  atm/K  mol p 3.1415926536 h 6.6260693  1034 J  sec c 2.99792458  108 m/sec Useful Conversion Factors and Relationships Length SI unit: Meter (m) kilometer 1000 meters 0.62137 mile meter 100 centimeters centimeter 10 millimeters nanometer 1.00  109 meter picometer 1.00  1012 meter inch 2.54 centimeter (exactly) Ångstrom 1.00  1010 meter Mass SI unit: Kilogram (kg) kilogram 1000 grams gram 1000 milligrams pound 453.59237 grams  16 ounces ton 2000 pounds Volume SI unit: Cubic meter (m3) liter (L) 1.00  103 m3 1000 cm3 1.056710 quarts gallon 4.00 quarts Energy SI unit: Joule (J) joule  kg  m2/s2  0.23901 calorie  C  V calorie  4.184 joules Pressure SI unit: Pascal (Pa) pascal N/m2  kg/m  s2 atmosphere  101.325 kilopascals  760 mm Hg  760 torr  14.70 lb/in2  1.01325 bar bar  105 Pa (exactly) Temperature SI unit: kelvin (K) K  273.15 °C K  °C  273.15°C ? °C  (5 °C/9 °F)(°F  32 °F) ? °F  (9 °F/5 °C)(°C)  32 °F Location of Useful Tables and Figures Atomic and Acids, Bases Molecular Properties and Salts   Atomic electron configurations Table 7.3 Common acids and bases Table 3.1   Atomic radii Figures 7.6, 7.9 Formation constants Appendix K   Bond dissociation enthalpies Table 8.9 Ionization constants for weak   Bond lengths Table 8.8  acids and bases Table 17.3, Appendix H, I   Electron Attachment Enthalpy Figure 7.11, Appendix F Names and composition of   Electronegativity Figure 8.11  polyatomic ions Table 2.4   Elements and their unit cells Figure 13.5 Solubility guidelines Figure 3.10   Hybrid orbitals Figure 9.3 Solubility constants Appendix J   Ionic radii Figure 7.12   Ionization energies Figure 7.10, Table 7.5 Miscellaneous Charges on common monatomic Thermodynamic    cations and anions Figure 2.18 Properties Common polymers Table 10.12   Enthalpy, free energy, entropy Appendix L Oxidizing and reducing agents Table 3.3   Lattice energies Table 13.2 Selected alkanes Table 10.2   Specific heat capacities Appendix D Standard reduction potentials Table 20.1, Appendix M kotz_48288_26_ EP5-7_SE.indd 12/1/10 9:53 AM Standard Atomic Weights of the Elements 2007  Based on relative atomic mass of its nuclear and electronic ground state.† Name Actinium* Aluminum Americium* Antimony Argon Arsenic Astatine* Barium Berkelium* Beryllium Bismuth Bohrium Boron Bromine Cadmium Cesium Calcium Californium* Carbon Cerium Chlorine Chromium Cobalt Copernicium Copper Curium* Darmstadtium Dubnium Dysprosium Einsteinium* Erbium Europium Fermium* Fluorine Francium* Gadolinium Gallium Germanium Gold Hafnium Hassium Helium Holmium Hydrogen Indium Iodine Iridium Iron Krypton Lanthanum Lawrencium* Lead Lithium Lutetium Magnesium Manganese Meitnerium Mendelevium* Mercury Symbol Atomic Number Ac 89 Al 013 Am 95 Sb 051 Ar 018 As 033 At 085 Ba 056 Bk 097 Be 004 Bi 083 Bh 107 B 005 Br 035 Cd 048 Cs 055 Ca 020 Cf 098 C 006 Ce 058 Cl 017 Cr 024 Co 027 Cn 112 Cu 029 Cm 096 Ds 110 Db 105 Dy 066 Es 099 Er 068 Eu 063 Fm 100 F 009 Fr 087 Gd 064 Ga 031 Ge 032 Au 079 Hf 072 Hs 108 He 002 Ho 067 H 001 In 049 I 053 Ir 077 Fe 026 Kr 036 La 057 Lr 103 Pb 82 Li 003 Lu 071 Mg 012 Mn 025 Mt 109 Md 101 Hg  80 Atomic Weight (227) 26.9815386(2) (243) 121.760(1) 39.948(1) 74.92160(2) (210) 137.327(7) (247) 9.012182(3) 208.98040(1) (272) 10.811(7) 79.904(1) 112.411(8) 132.9054519(2) 40.078(4) (251) 12.0107(8) 140.116(1) 35.453(2) 51.9961(6) 58.933195(5) (285) 63.546(3) (247) (281) (268) 162.500(1) (252) 167.259(3) 151.964(1) (257) 18.9984032(5) (223) 157.25(3) 69.723(1) 72.64(1) 196.966569(4) 178.49(2) (270) 4.002602(2) 164.93032(2) 1.00794(7) 114.818(3) 126.90447(3) 192.217(3) 55.845(2) 83.798(2) 138.90547(7) (262) 207.2(1) 6.941(2) 174.9668(1) 24.3050(6) 54.938045(5) (276) (258) 200.59(2) †The atomic weights of many ele­ments can vary depending on the origin and treatment of the sample This is particularly true for Li; commercially available lithium-containing materials have Li atomic weights in the range of 6.939 and 6.996 The uncertainties in atomic weight values are given in parentheses following the last significant figure to which they are attributed kotz_48288_26_ EP5-7_SE.indd Name Molybdenum Neodymium Neon Neptunium* Nickel Niobium Nitrogen Nobelium* Osmium Oxygen Palladium Phosphorus Platinum Plutonium* Polonium* Potassium Praseodymium Promethium* Protactinium* Radium* Radon* Rhenium Rhodium Roentgenium Rubidium Ruthenium Rutherfordium Samarium Scandium Seaborgium Selenium Silicon Silver Sodium Strontium Sulfur Tantalum Technetium* Tellurium Terbium Thallium Thorium* Thulium Tin Titanium Tungsten Ununhexium Ununoctium Ununpentium Ununquadium Ununseptium Ununtrium Uranium* Vanadium Xenon Ytterbium Yttrium Zinc Zirconium 12 C  12, where Symbol Mo Nd Ne Np Ni Nb N No Os O Pd P Pt Pu Po K Pr Pm Pa Ra Rn Re Rh Rg Rb Ru Rf Sm Sc Sg Se Si Ag Na Sr S Ta Tc Te Tb Tl Th Tm Sn Ti W Uuh Uuo Uup Uuq Uus Uut U V Xe Yb Y Zn Zr 12 C is a neutral atom in Atomic Number Atomic Weight 42 95.96(2) 060 144.242(3) 10 20.1797(6) 093 (237) 028 58.6934(4) 041 92.90638(2) 007 14.0067(2) 102 (259) 076 190.23(3) 008 15.9994(3) 046 106.42(1) 015 30.973763(2) 078 195.084(9) 094 (244) 084 (209) 019 39.0983(1) 059 140.90765(2) 061 (145) 091 231.03588(2) 088 (226) 086 (222) 075 186.207(1) 045 102.90550(2) 111 (280) 037 85.4678(3) 044 101.07(2) 104 (267) 062 150.36(2) 021 44.955912(6) 106 (271) 034 78.96(3) 014 28.0855(3) 047 107.8682(2) 011 22.98976928(2) 038 87.62(1) 016 32.065(5) 073 180.94788(2) 043  (98) 052 127.60(3) 065 158.92535(2) 081 204.3833(2) 090 232.03806(2) 069 168.93421(2) 050 118.710(7) 022 47.867(1) 074 183.84(1) 116 (292) 118 (294) 115 (228) 114 (289) 117 (294) 113 (284) 92 238.02891(3) 023 50.9415(1) 054 131.293(6) 070 173.054(5) 039 88.90585(2) 030 65.38(2) 040 91.224(2) *Elements with no stable nuclide; the value given in parentheses is the atomic mass number of the isotope of longest known half-life However, three such ele­ments (Th, Pa, and U) have a characteristic terrestial isotopic composition, and the atomic weight is tabulated for these http://www.chem.qmw 12/1/10 9:53 AM ... Odor of Ester O CH3 CH3CO2H CH3CHCH2CH2OH CH3COCH2CH2CHCH3 acetic acid 3-methyl-1-butanol 3-methylbutyl acetate Banana O CH3CH2CH2CO2H CH3CH2CH2CH2OH CH3CH2CH2COCH2CH2CH2CH3 butanoic acid 1-butanol... amines, putrescine and cadaverine, add to the odor of urine, rotten meat, and bad breath H2NCH2CH2CH2CH2NH2 H2NCH2CH2CH2CH2CH2NH2 putrescine 1,4-butanediamine cadaverine 1,5-pentanediamine The smallest... acid palmitic acid stearic acid oleic acid CH3(CH2)10CO2H CH3(CH2)12CO2H CH3(CH2)14CO2H CH3(CH2)16CO2H CH3(CH2)7CHPCH(CH2)7CO2H The reaction of fats and oils with methanol (in the presence of a catalyst
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