EK 1001 OChem

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Table of Contents Questions Page Molecular Structure 1- 209.- ~~ Structural Formula · -51 Bonding 52 - 118 Stereochemistry 119.- 209 14 Alkanes, Alcohols, and Substitutions 210- 496 25 Alkanes 210- 393 25 Alcohols and Substitutions 394- 496 44 Carbonyls and Amines 497- 766 54 Aldehydes and Ketones 497- 597 54 Carboxylic Acids and Derivatives 598 -766 64 Biochemistry and Lab Techniques 767- 766 '83 Fatty Acids and Amino Acids 767- 853 83 Carbohydrates 854- 910 93 Lab Techniques 911 - 1001 99 Answers and Explanations 109 PHYSICAL SCIENCES DIRECTIONS Most questions in the Physical Sciences test are organized into groups, each preceded by a descriptive passage After studying the passage, select the one best answer to each question in the group Some questions are not based on a descriptive passage and are' also independent of each other You must also select the one best answer to these questions If you are not certain of an answer, eliminate the alternatives that you know to be incorrect and then select an answer from the remaining alternatives Indicate your selection by blackening the corresponding oval on your answer document A periodic table is provided for your use You may consult it whenever you wish PERIODIC TABLE OF THE ELEMENTS , - ; - H He 1.0 Li Be 6.9 11 9.0 "12 Na Mg 4.0 10 B c N F Ne 10.8 13 12.0 14 14.0 15 16.0 16 19.0 17 20.2 18 Cl Ar 35.5 35 39.9 36 AI Si p s 27.0 31 28.1 32 31.0 33 32.1 34 23.0 19 24.3 20 21 22 25 26 27 28 29 30 Ca Sc Ti v 24 K Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr 39.1 37 40.1 38 45.0 39 47.9 40 50.9 41 52.0 42 55.8 44 58.9 45 58.7 46 63.5 47 65.4 48 69.7 49 72.6 50 74.9 51 79.0 52 79.9 53 83.8 54 Rb Sr y 54.9 43 Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe 85.5 55 87.6 56 88.9 57 91.2 72 92.9 73 (98) Cs Ba La* Hf Ta 23 95.9 74 w 75 Re 101.1 102.9 106.4 107.9 112.4 114.8 118.7 121.8 127.6 126.9 131.3 86 83 80 81 82 84 85 76 77 78 79 Os lr Pt Au Hg Tl Pb Bi Po At Rn 132.9 137.3 138.9 178.5 180.9 183.9 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 (209) (210) (222) 104 105 106 107 108 109 88 89 87 Fr Ra Act Unq Unp Unh Uns Uno Une (223) 226.0 227.0 (261) (262) (263) -(262) (265) (267) * 58 59 60 Ce Pr Nd 62 63 64 65 66 67 68 Pm Sm Eu Gd Tb Dy Ho Er 61 70 71 Tm Yb 69 Lu 140.1 140.9 144.2 (145) 150.4 152.0 157.3 158.9 162.5 164.9 167.3 168.9 173.0 175.0 100 101 90 102 103 99 91 92 93 94 95 96 97 98 Th Pa u Np Pu Am Cm Bk Cf Es Fm Md No Lr 232.0 (231) 238.0 (237) (244) (243) (247) (247) (251) (252) (257) (258) (259) (260) Copyright © 2006 Examkrackers, Inc Molecular Structure Structural Formula What is the CH3CH2CHO? correct Lewis c A H H"O" :: H:c:c:c:H A B C D D H H"O" H:c:c::c:H A attached to the same carbon H H H:C: C::c::Q:H D attached directly to each other Refer to the Fischer projection below to answer questions 8-10 c HOrCHbH HO OH HO OH H:Cl:N D H:C::N CH3 H:CHN A Lewis base donates a pair of electrons Which of the In the Fischer projection, the hydroxide groups are: A coming out of the page on the right side and into following molecules could be a Lewis base? the page on the left B coming out of the page on the left side and into the page on the right C coming out of the page D going into the page A CH4 B NH3 C AlCh D BH3 In the Newman projection, the hydroxide group and the methyl group are: H H :H::c::N: B The largest carbon in the structure The second carbon along the axis of the bond The first carbon along the axis of the bond The radius ofthe bond B attached to different carbons 1, C attached to carbons with no hydrogens attached What is the correct Lewis dot structure for HCN? A for H H H H stnicture H H g:H H:c:c:c: H H B dot In the Newman projection, what does the intersection of the three lines represent? Which of the following molecules could NOT be a Lewis base? In the Fischer projection, the methyl groups are: A coming out of the page on the top and into the page on the bottom B coming out of the page on the top and into the page on the bottom C coming out of the page D going into the page A NH(CH3)2 B NH/ C HzO D OH- 10 In the Fischer projection, what the intersections of the vertical and horizontal lines represent? Refer to the Newman projection below to answer questions 5-7 A rotation of the bond B carbon atoms C double bonds D nothing In the Newman projection, what does the circle represent? A B C D The largest carbon in the structure The second carbon along the axis of the bond The first carbon along the axis of the bond The radius of the bond Copyright© 2006 EXAMKRACKERS, Inc 1001 Questions in MCAT Organic Chemistry Refer to the dash-line-wedge formula below to answer questions 11-13 11 In the dash-line wedge formula what atom(s) is (are) coming out of the page? 15 Which of the following structures is a ketone? OH B D H,N~ I Cl II Br m c A H A B C D I only II only IIandiD Iandill HOrr 16 What is the name of the functional group contained iJJ the structure shown below? 12 In the dash-line wedge formula what atom(s) is (are) going back into the page? I Cl II CH3 A B C D m H A B C D I only II only IIandiD Iandill ether ester carboxylic acid alcohol 17 What is the name of the functional group contained i.J the structure shown below? 13 In the dash-line wedge formula what atom(s) is (are) in the plane of the page? I CH3 II Br A B C D m H A B C D Ionly II only IIandiD Iandill 14 Which of the following structures is an amide? c A ~~ OH ether ester carboxylic acid alcohol 18 Isoamylacetate is a honeybee pheromone that i released on the skin when a bee stings its victim Thi pheromone has a sweet smell and attracts other bees join the fight The structure of isoamylacetate is show below What functional group does it contain? A B C D ether ester carboxylic acid alcohol Copyright© 2006 EXAMKRACKERS, Inc Molecular Structure 22 How many amide groups are present in luminol? question 21 for the structure? 19 Tetrahydrofuran (THF) is a common solvent for synthetic reactions because it is an ether Ethers are relatively inert so they not participate in the reaction Which of the following structures is THF? A B c D c A Q B See 23 Menthol is one of the molecules responsible for the mint odor What functional groups are present in menthol? >-p D I, HO A cycloalkane and alkene B cycloalkene and alcohol C cycloalkane and ether D cycloalkane and alcohol 24 Similar in structure to menthol is limonene which is responsible for the lemon odor found in natural products What is the difference in functional groups between these two structures? 20 Aspirin is the common name for acetylsalicylic acid The structure is shown below, what three functional groups are present in this molecule? >-0A B C D A Menthol has an alcohol and Iimonene has an alkyne B Menthol has an alcohol and limonene has an alkene C Menthol has an ether and limonene has an alkyne D Menthol has an ether and limonene has an alkene ether, aromatic ring, carboxylic acid ester, phenyl, carboxylic acid alkene, aromatic ring, carbooxylic acid alcohol, ether, carboxylic acid 25 Eugenol is a dental anesthetic that is isolated from oil of cloves The structure is shown below What functional groups are present in this toothache remedy? 21 Luminol is a compound used by the police to detect the presence of dried blood Upon oxidation, luminol emits a green light in the presence of a metal ion such as the Fe ion found in blood The structure of luminol is shown below How many amine groups are present in this molecule? H2C=C-C~OH H H "=(OCH3 A B C D aromatic ring, alkene, alcohol, and ether cycloalkyl ring, alkene, alcohol, and ester aromatic ring, alkyne, ether, and ester aromatic ring, alkene, alcohol, and ester A B c D 3 Copyright© 2006 EXAMKRACKERS, Inc 1001 Questions in MCAT Organic Chemistry 26 When eugenol (shown in question 25) is isolated from the clove flower buds, acetyleugenol (shown below) is also isolated and must be separated from the eugenol What is the difference between these two compounds? 31 What is the index of hydrogen deficiency for structure shown below? ~ H2c=c-c -r-\- o_}j _ H H2 "==(- CH OCH3 A The ether of eugenol is converted to an ester in acetyleugenol B The alcohol of eugenol is converted to an ether in acetyleugenol C The ester of eugenol is converted to an ether in acetyleugenol D The alcohol of eugenol is converted to an ester in acetyl eugenol A B c D 32 What is the index of hydrogen deficiency for structure shown below? Br A 27 What is the index of hydrogen deficiency for the molecular formula C8H 12? A B c D 28 What is the index of hydrogen deficiency for the molecular formula CsOzH12? B c D 33 A brightener that is used for white shirts is Calcoflu White MR The structure of this whitener is sho~ below How many amine functionalities are present this molecule? A B c D 29 What is the index of hydrogen deficiency for the molecular formula C80zH11Br? A B c D 30 What is the index of hydrogen deficiency for the structure shown below? A B c 12 D 14 34 How many degrees of unsaturation (index of hydrogt: deficiency) are in each phenyl ring on the end of t1 calcofluor shown in question 33? A B Z c D A B c D 4 Copyright© 2006 EXAMKRACKERS, Inc Molecular Structure 35 Another brightener that is used on wool and nylon fabrics is 7-dimehtylamino-4-methylcoumarin What functional groups are present in this brightener? ro (CzHshN A · B C D ::::::: 39 Ethanol reacts with sulftn:ic acid at 140°C to form an ether The ether formed would be: A B C D diethylether 1-ethyne 1-propene ethanal 40 Alcohols are converted to esters using carboxylic acids Using anhydrides is a better way to achieve this conversion Which reagent would best convert octanol to octyl acetate, an ester that has a fruity odor? aromatic ring, alkene, ketone, ether and amide aromatic ring, cycloalkene, ketone, and ether aromatic ring, cycloalkene, ester, and amine aromatic ring, cycloalkene, ester, and amide 'i, A C 36 What is the IUPAC name for the structure shown below? B A B C D 38 D )lOCH3 41 Bilirubin is a bile pigment found in human gallstones The structure of bilirubin is shown below How many amide functional groups are present in this pigment? H C=CH2 4-isopropyl-6-octanol 5-isopropyl-3-octanol 5-isopropyl-3-hexanol 4-2-butanol-5-methylhexane CH2CHzCOOH Which structure below is the correct structure of 1ethyl-3-(1, 1,3-trimethylbutyl)cyclooctane? A ~ 2,2-dimethyl-3-n-butylpentane 4,4-dimethyl-3-n-butylpentane 5-tert-butylheptane 3-tert-butylheptane 37 What is the IUPAC name for the structure shown below? A B; C D ~OH )lOH CH2CH2COOH A C B c D B 42 How many amine groups are found in bilirubin (structure shown in question 41)? D A B c D 43 How many carboxylic acid groups are found in bilirubin (structure shown: in question41)? A B c D Copyright© 2006 EXAMKRACKERS, Inc 1001 Questions in MCAT Organic Chemistry 44 2,4-dinitrohydrazine reacts With ketones and aldehydes to form a 2,4-dinitrohyrazone The 2,4-DNP •test is used to determine if an unknown compound is an aldehyde or ketone Which reagent would produce a positive 2,4-DNP test? 48 In the reaction shown below, what is the functional group conversion·that takes place?· oyo ~c~ A B C D OH alkane to aldehyde cycloalkane to cycloketone alkane to cycloalkane cycloalkane to cycloether ;, B 49 The following Newman projection looks down which ~ bond of 1-choropentane, according to IUPAC carbon numbers? CH3 H NHz H Hxp:H 45 Given the information in question 44, which of the following compounds would be the best solvent for the 2,4-DNP test? CHzCH2Cl A the bond between Cl and C2 B the bond between C2 and C3 C the bond between C3 and C4 D the bond between C4 and CS I acetone n m I ethanol heptanal A I only llonly c llandillonly D Iandillonly B 50 Which structure is the Fischer projection for the structure shown below? 46 If 1-methylcyclopentene undergoes hydration to form an alcohol, what would be the product? A c c A CHO CHO ~OH B B.:& H 47 When 1-chloro-3-methylpentane is reacted with excess ammonia the halogen is replaced by an amine group What is the structure of the product of this reaction? A B HO+H CH3 CH3 H' c OH H ~Cl Copyright© 2006 H EXAMKRACKERS, Inc D H~&, OHC Molecular Structure 56 What is the hybridization of the sigma bond between the carbon ·atom and the nitrogen atom in HCN? 51 Which structure is the dash-line-wedge fonnula for the structure shown below? H~ r~H A B C D CH3 c A 57 What is the fonnal charge on the nitrogen atom in HCN? H~·H CH3 ~ OHC A B HO H B.:$ H H sp sp2 sp3 sp3d c ;, D D 58 Which bond is the most stable bond? H A B C D OH signia bond pi bond in an alkene pi bond in an alkyne pi bond in a carbonyl H 59 What types of bonds are found in an alkyne functional group? Bonding A one sigma bond and one pi bond B two sigma bond and one pi bond C one sigma bond and two pi bonds that are perpendicular to each other D one sigma bond and two pi bonds that are parallel to each other 52 What force is responsible for the bonds between atoms? A B C D Dipole-dipole Hydrogen bonding Gravitational Electrostatic Refer to the Lewis Dot structure shown below to answer questions 53-57 Average bond energies are shown in the table below Use the table to answer questions 60-61 •• H:c liN Bond 53 How many electrons are involved in the sigma bond between the carbon atom and the nitrogen atom? c-c c c A B c C=C D A 60 kcal mort B 80 kcal mort c 150 kcal mort D 200 kcal mort pi bond and two sigma bonds pi bonds and one sigma bond pi bonds and zero sigma bonds sigma bonds and zero pi bonds 61 Based on the values in the table, what is the approximate average bond energy for each pi bond? 55 How many electrons does the N atom contribute to the pi bonds? A 60 kcal mort B 80 kcal mort c 150 kcal mort D 200 kcal mort A B c 83 146 200 60 Based on the values· in· the table, what is the approximate average bond energy for each sigma bond? 54 What types of bonds exist between the C atom and the N atom in HCN? A B C D Average Bond Energy kcalmort D Copyright© 2006 EXAMKRACKERS, Inc 1001 Questions in MCAT Organic Chemistry 68 The bond angle formed by HI, C2, and H3 in aspartame is: 62 The energy of a 2sp hybridized orbital for a carbon atom is A 180° B 120° A higher in energy than the 2s atomic orbital and lower in energy than the 2p atomic orbital B higher in energy than the 2p atomic orbital and lower in energy than the 2s atomic orbital C higher in energy than both the 2s and the 2p atomic · orbitals D lower in energy than both the 2s and the 2p atomic orbitals c 109° D 90° 69 The bond angle formed by 04, C5, and 06 in aspartame is: A 180° B 120° c 109° D 90° 63 The overlap of what two orbitals form the pi bond between carbon atoms in an alkene? A B C D two p orbitals two sp2 orbitals two sp3 orbtials two s orbitals 70 The bond angle formed by C7, N8, and H9 in aspartame is: A 180° B 120° c 109° D 90° 64 How much s character does an sp3 hybridized orbital have? A no s character B 25% c 33.3% D 50% Cocaine is a stimulant that is isolated from coca leaves Refer to the structure of cocaine shown below to answer questions 71-80 Refer to the structure of aspartame, an artificial sweetener, to answer questions 65-70 yooH ~-~H~l2 CH2 H9 CH2 06 H I 11· I 71 II I H2N-c-c-N-c-c o-c-H H ·;, H Aspartame 12 ' I J J ~11 10 H 1 H3 65 The hybridization of the C2 carbon in aspartame is: 71 The hybridization of the C9 carbon in cocaine is: A sp B sp C sp D sp3d A sp B sp C sp D sp 3d 66 The hybridization of the C5 carbon in aspartame is: 72 The hybridization of the N8 nitrogen in cocaine is: A sp A B C D B sp2 C sp3 D sp 3d 67 The hybridization of the N8 nitrogen in aspartame is: sp sp sp3 sp 3d 73 The hybridization of the 03 oxygen in cocaine is: A sp B sp2 C sp3 D sp3d A sp B sp2 C sp D sp3d Copyright© 2006 EXAMKRACKERS, Inc ~ ,I J ~ ~ r.~ l ' ···~I····· ' ~~ I.f:1 s,, 1i " 1001 Questions in MCAT Organic Chemistry 610 611 c c 612 D 613 A 614 C 615 A 616 c 617 A 618 c 619 B 620 c 621 c 622 B 623 c 624 B 625 D 626 D 627 c 628 c 629 A 630 A 631 D 632 633 634 635 A A B D 636 B 637 638 639 640 641 642 643 644 645 B A B c B c c B c 646 B 647 A 648 B Since the electron withdrawing group is closer to the acidic hydrogen, it has a greater stabilizing effect According to the table, an addition of a Cl atom lowers the pK of an acid Thus, the pK of 2,2-dichloroethanoic acid will be between one Cl atom and three Cl atoms Answer C is the only value that fits this criteriaon Both carbon oxygen bonds are involved in the resonance of the negative charge The bond length is between the single and double bond · An acid chloride is more reactive than an ester so the alcohol will combine with the acid chloride to form an ester by displacing the chloride atom Similar to the alcohol formation of an ester, an amine combined with a carboxylic acid forms an amide Alcohols are oxidized to carboxylic acids · Thionyl chloride (SOCb) is the reagent that converts butanoic acid to butyl chloride because it provides a nucleophilic · · chloride atom An acid chloride plus a carboxylate ion forms an anhydride The carboxylic acid, ester and amide are more stable than the anhydride, so they will not react Ethanol will react to displace the OH and form the ethyl ester An alcohol and an acid combine to form an ester The oxygen in ethanol is nucleophilic and attacks the carbonyl carbon The oxygen in the hydroxide group of the acid leaves as water Beta keto carboxylic acids can decarboxylate releasing C02 • An anhydride has an oxygen atom between two carbonyl carbons The anhydride is formed because it is more reactive than the acid, which enhances the reaction with hydrazine Hydrazine is a nucleophile and sigma bonds are substituted for sigma bonds Fewer bonds to oxygen are present in the product than in the reactant All three will increase the formation of an ester Increasing the concentration of alcohol increases the concentration of a reactant Anhydrides are more reactive than carboxylic acids leading to more product Acid catalyzes the reaction The same product is formed in each reaction so answers A and B are eliminated Acid chlorides are more reactive the carboxylic acids so they not require a catalyst The acid protonates the OH of the carboxylic acid converting it to water, a good leaving group It also activates the electrophile by protonating the carbonyl oxygen, which makes the carbonyl carbon more electron deficient The Grignard reagent is a strong nucleophile that replace one sigma bond with another sigma bond; therefore, the reaction is a nucleophilic substitution The conjugation is not stabilizing any charges so it has nothing to with the relative reactivities, eliminating answers C and D Benzophenone must be more reactive causing the Grignard reagent to preferentially react with the benzophenone over the methyl benzoate The tertiary alcohol cannot be oxidized to any carbonyl, so all that can be done is removal of the proton by a base Both benzophenone and methyl benzoate not have acidic protons, eliminating answers B and C Triphenylcarbinol is more acidic than ethanol because it has extensive resonance stabilization of the conjugate base's negative charge The acetate ion is electron rich so it is a nucleophile The ester will be optically active because the reaction will be an SN2 mechanism with inversion of stereochemistry The acetate ion can also be a base and remove a hydrogen atom to start a dehydrohalogenation Because the reaction is a SN2 reaction, the rate determining step depends on the concentration of both the electrophile and the nucleophile (I and II) Raising the temperature almost always speeds up a reaction (III) The acid chloride will be more reactive than the carboxylic acid, eliminating answers C and D The amide has two ethyl groups attached, so diethyl amine is required · Beta keto esters are subject to decarboxylation reactions, and answer B is the only beta keto ·ester The first step of the reaction scheme is necessary to activate the electrophile b5' creating a more reactive species The anilide has an amine group next to a carbonyl making it an amide The S02Cl provides a strong nucleophilic chloride so that the chloride ion can substitute for the hydroxide group The lone pair of electrons on the nitrogen atom is nucleophilic and attacks the electrophilic carbonyl carbon The nucleophilic amine attacks the carbonyl carbon and replaces the chloride atom The bromine atom is electron withdrawing making the carbonyl carbon more electrop4ilic There is no amide product eliminating answer A The triethylamine contains a proton in the product indicating that it has functioned as a base ·Resonance stabilization of the conjugate baseanion,increases the.acidity_of the.phenol.hydr_og~n.QD.~Il;l,e,_f.QlQrin~ ~_;. atoms are electron withdrawing also stabilizing the negative charge (I) · The oxygens next to the carbonyls are attached to alkyl groups The hydrogen is removed from the phenol to make an electron rich anion that can attack the electrophilic carbonyl The name indicates the plane of symmetry that 'is in the middle of the molecule 136 Copyright© 2006 EXAMKRACKERS, Inc: Answers and Explanations 649 B 650 B 651 B 652 c The intennediate is a peroxide with two oxygen atoms linked in a sigma bond The presence of the extra oxygen indicates a higher oxidation state Also hydrogen peroxide is an oxidizing agent · · Decarboxylation indicates that the reactant loses C02, so answers A and C are eliminated The product is a Z alkene so the phenyl groups need to be on the same side, answer B A ketone is fonned in the place of a carboxylic acid The ketone is at a lower oxidation state The name indicates that the benzoyl group is a substituent on benzoic acid The group is circled below 'i, 653 B 654 c 655 c 656 A 657 D 658 B 659 c 660 B 661 662 663 664 665 D A B D B 666 667 668 669 B D B A 670 A 671 D 672 c 673 A :J74 :J75 576 )77 )78 A B B A 'i79 c c '180 A '181 B '182 D '183 D The carbonyl is the electrophile in the reaction The acid provides a proton to turn the hydroxide into a good leaving group, then the proton is regenerated in the last step of the reaction Based on the generic reaction, the OR' attaches to the carbonyl which would give the product in answer
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