Lecture Presentation Chapter 13 Alcohols, Phenols, Thiols, and Ethers Karen C Timberlake General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chapter 13 Alcohols, Phenols, Thiols, and Ethers Anesthesia is typically administered by a nurse anesthetist who provides care before, during, and after a medical procedure A nurse anesthetist gives medications to keep a patient asleep and pain-free while monitoring the patient’s vital signs General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chapter 13 Readiness Core Chemistry Skills • Naming and Drawing Alkanes (12.2) General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc 13.1 Alcohols, Phenols, Thiols, and Ethers Functional groups such as OH • an alcohol contain a hydroxyl CH3 OH group (— OH) Phenol Methanol • a phenol contain a hydroxyl group (— OH) bonded to a benzene ring CH3—CH2—SH • a thiol contain an — SH group Learning Goal Give the IUPAC and common names for alcohols, phenols, and thiols; draw their condensed and line-angle structural formulas General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Alcohols, Phenols, and Thiols Core Chemistry Skill Identifying Alcohols, Phenols, and Thiols General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Naming Alcohols • In the IUPAC system, replace the e with ol • With common names, use the name of the alkyl group followed by alcohol Core Chemistry Skill Naming Alcohols and Phenols General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake â 2016 Pearson Education, Inc Naming Alcohols For alcohols with three or more carbon atoms, number the carbons in the chain to give the position of the — OH group and any substituents on the chain • An alcohol with two — OH groups is named as a diol An alcohol with three — OH groups is named as a triol General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Naming Cyclic Alcohols A cyclic alcohol is named as a cycloalkanol • If there are substituents, the ring is numbered from carbon 1, which is the carbon attached to the — OH group • Compounds with no substituents on the ring not require a number for the hydroxyl group General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Naming Phenols • The term phenol is the IUPAC name when a hydroxyl group (— OH) is bonded to a benzene ring • When there is a second substituent, the benzene ring is numbered starting with carbon 1, bonded to the — OH group • The terms ortho, meta, and para are used for the common names of simple phenols • The common name cresol is also used for methylphenols General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Guide to Naming Alcohols General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Oxidation and Reduction In organic chemistry, • oxidation reactions increase the number of carbon–oxygen bonds by the addition of oxygen or a loss of hydrogen atoms • reduction reactions reduce the number of bonds between carbon and oxygen atoms Core Chemistry Skill Writing Equations for the Oxidation of Alcohols General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Oxidation of 1° Alcohols Alcohols undergo oxidation, increasing the number of carbon and oxygen bonds To indicate the process of oxidation, [O] is placed over the reaction arrow Primary alcohols are oxidized to produce an aldehyde bond to O bonds to O [O] 1° alcohol General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake aldehyde © 2016 Pearson Education, Inc Oxidation of 1° Alcohols Aldehydes can further oxidize to produce a carboxylic acid bond to O bonds to O [O] aldehyde General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake carboxylic acid © 2016 Pearson Education, Inc Oxidation of 2° Alcohols Secondary alcohols are oxidized to produce a ketone bond to O bonds to O [O] 2° alcohol General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake ketone © 2016 Pearson Education, Inc Oxidation of 3° Alcohols Tertiary alcohols not readily oxidize because there is no hydrogen atom on the carbon bonded to the — OH group [O] no product formed no H to oxidize 3° alcohol General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chemistry Link to Health: Methanol Poisoning Methanol is • also known as methyl alcohol • highly toxic and found in windshield washer fluid, Sterno, and paint strippers • rapidly absorbed and oxidized to formaldehyde and then formic acid [O] methyl alcohol [O] formaldehyde General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake formic acid © 2016 Pearson Education, Inc Oxidation of Thiols When thiols undergo oxidation, • an H atom is lost from each of two — SH groups • the product is a disulfide Protein in hair is cross-linked by disulfide bonds found in the amino acid cysteine CH3—S—H + H—S—CH3 General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake [O] CH3—S—S—CH3 + H2O © 2016 Pearson Education, Inc Chemistry Link to Health: Oxidation of Alcohol in the Body Ethanol • acts as a depressant and kills or disables more people than does any other drug • consumption can be analyzed by using a breathalyzer • is metabolized by a social drinker at a rate of 12–15 mg/dL per hour • is metabolized by an alcoholic at a rate of 30 mg/dL per hour General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chemistry Link to Health: Oxidation of Alcohol in the Body The acetaldehyde produced from ethanol in the liver is further oxidized to acetic acid, which is converted to carbon dioxide and water in the citric acid cycle Liver enzymes can eventually break down ethanol, but the aldehyde and carboxylic acid intermediates can cause considerable damage to liver cells General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chemistry Link to Health: Oxidation of Alcohol in the Body General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Study Check Select the product for the oxidation of [O] A C CO2 + H2O General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake B D © 2016 Pearson Education, Inc Solution Select the product for the oxidation of [O] The correct answer is B General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Study Check Select the product when CH3–CH2–CH2–OH undergoes each of the following reactions: [O] [O] A B CO2 + H2O C D General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Solution Select the product when CH3–CH2–CH2–OH undergoes each of the following reactions: [O] [O] C D General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Concept Map General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc ... CH3 General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Chemistry Link to Health: Alcohols and Phenols General, Organic, and Biological. .. Pearson Education, Inc Alcohols, Phenols, and Thiols Core Chemistry Skill Identifying Alcohols, Phenols, and Thiols General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake... found in many solvents and paint removers • is oxidized to formaldehyde when ingested and can cause headaches, blindness, and death General, Organic, and Biological Chemistry: Structures of Life,