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Organic Chemistry, 7e by L. G. Wade, Jr. Chapter 10 Structure and Synthesis of Alcohols Christine Hermann Radford University Radford, VA Copyright © 2010 Pearson Education, Inc. 10.1 Classify 2,3-dimethyl-2butanol. a. b. c. d. 0o alcohol 1o alcohol 2o alcohol 3o alcohol 10.1 Answer a. b. c. d. 0o alcohol 1o alcohol 2o alcohol 3o alcohol The carbon bearing the –OH has three other carbons attached to it. 10.2 Give the common name for (CH3)3CCH2OH. a. b. c. d. e. Tert-pentyl alcohol Tert-butyl alcohol Isopentyl alcohol Isobutyl alcohol Neopentyl alcohol 10.2 Answer a. b. c. d. e. Tert-pentyl alcohol Tert-butyl alcohol Isopentyl alcohol Isobutyl alcohol Neopentyl alcohol 10.3 Name H2C OH a. b. c. d. 1-Butanol 2-Butanol Butane-1,2-diol Butane-1,2-ol H C OH CH2CH3 10.3 Answer a. b. c. d. 1-Butanol 2-Butanol Butane-1,2-diol Butane-1,2-ol Butane is the longest chain; the OHs are in the 1 and 2 positions. 10.4 Name a. b. c. d. 1-Ethylphenol 2-Ethylphenol 3-Ethylphenol 4-Ethylphenol OH CH2CH2CH3 10.4 Answer a. b. c. d. 1-Ethylphenol 2-Ethylphenol 3-Ethylphenol 4-Ethylphenol Phenol is a benzene with an OH attached and is in position one. 10.5 Give the name of the alcohol that is in beer and wine. a. b. c. d. Methanol Ethanol 2-Propanol 1-Propanol 10.5 Answer a. b. c. d. Methanol Ethanol 2-Propanol 1-Propanol The active ingredient in beer and wine is ethanol. 10.6 Give the common use for ethane-1,2-diol. a. b. c. d. Drinking alcohol Rubbing alcohol Vinegar Antifreeze 10.6 Answer a. b. c. d. Drinking alcohol Rubbing alcohol Vinegar Antifreeze Ethane-1,2-diol (ethylene glycol) is used as antifreeze; it is very toxic to animals. 10.7 a. b. c. d. Na CH3CH2CH2OH NaCH2CH2CH2OH CH3CH(Na)CH2OH CH3CH2CH(Na)OH CH3CH2CH2ONa 10.7 Answer a. b. c. d. NaCH2CH2CH2OH CH3CH(Na)CH2OH CH3CH2CH(Na)OH CH3CH2CH2ONa Sodium reacts with alcohols to form alkoxides. 10.8 1. H2C=O CH3CH2MgBr + 2. H3O a. b. c. d. CH3CH2CH2OH CH3CH2OCH3 CH3CH2OH CH3CH2OMgBr 10.8 Answer a. b. c. d. CH3CH2CH2OH CH3CH2OCH3 CH3CH2OH CH3CH2OMgBr The Grignard reagent adds to the aldehyde to form an alcohol. 10.9 Identify the alcohol formed when a Grignard reagent adds to a ketone. a. b. c. d. 0o alcohol 1o alcohol 2o alcohol 3o alcohol 10.9 Answer a. b. c. d. 0o alcohol 1o alcohol 2o alcohol 3o alcohol A Grignard reagent adds to a ketone to give, after hydrolysis, a 3o alcohol. O 10.10 C CH3CH2 a. b. c. d. 1. 2 CH3MgBr Cl 3-Methyl-3-pentanol 2-Methyl-2-butanol 2-Methyl-3-butanol 2-Methyl-3-pentanol 2. H3O+ 10.10 Answer a. b. c. d. 3-Methyl-3-pentanol 2-Methyl-2-butanol 2-Methyl-3-butanol 2-Methyl-3-pentanol Two methyls add to the carbonyl carbon, followed by hydrolysis. O 1. 2 CH3MgBr 10.11 C CH3CH2 a. b. c. d. OCH2CH3 2. H3O+ 3-Methyl-3-pentanol + methanol 2-Methyl-2-butanol + ethanol 2-Methyl-3-butanol + methanol 2-Methyl-3-pentanol + ethanol 10.11 Answer a. b. c. d. 3-Methyl-3-pentanol + methanol 2-Methyl-2-butanol + ethanol 2-Methyl-3-butanol + methanol 2-Methyl-3-pentanol + ethanol Two methyls add to the carbonyl carbon, followed by hydrolysis. The ethoxide is protonated. O 10.12 1. CH3CH2MgCl a. b. c. d. CH3CH2CH(OH)CH3 CH3CH2OH CH3CH2CH2OH CH3CH2CH2CH2OH 2. H3O+ 10.12 Answer a. b. c. d. CH3CH2CH(OH)CH3 CH3CH2OH CH3CH2CH2OH CH3CH2CH2CH2OH Grignard reagents add to epoxide to yield an alcohol that is two carbons longer. 10.13 Give the reason why Grignard reactions must have dry glassware. a. Grignard reagents react vigorously and irreversibly with water. b. Magnesium dissolves in water. c. The alkyl halide dissolves in water. d. Grignard reagents do not react with water. 10.13 Answer a. Grignard reagents react vigorously and irreversibly with water. b. Magnesium dissolves in water. c. The alkyl halide dissolves in water. d. Grignard reagents do not react with water. 10.14 Identify the compounds that sodium borohydride reduces. a. Aldehydes and ketones b. Esters and carboxylic acids c. Aldehydes, ketones, esters, and carboxylic acids d. Alkenes and alkynes 10.14 Answer a. Aldehydes and ketones b. Esters and carboxylic acids c. Aldehydes, ketones, esters, and carboxylic acids d. Alkenes and alkynes O 10.15 1. NaBH4 C H2C a. b. c. d. CH CH2COOH CH2=CHCH(OH)COOH CH3CH2CH(OH)COOH CH2=CHCH(OH)CH2OH CH3CH2CH(OH)CH2OH 2. H3O+ 10.15 Answer a. b. c. d. CH2=CHCH(OH)COOH CH3CH2CH(OH)COOH CH2=CHCH(OH)CH2OH CH3CH2CH(OH)CH2OH Sodium borohydride reduces ketones, but does not reduce alkenes or carboxylic acids. 10.16 Identify the compounds that lithium aluminum hydride reduces. a. Aldehydes and ketones b. Esters and carboxylic acids c. Aldehydes, ketones, esters, and carboxylic acids d. Alkenes and alkynes 10.16 Answer a. Aldehydes and ketones b. Esters and carboxylic acids c. Aldehydes, ketones, esters, and carboxylic acids d. Alkenes and alkynes O 10.17 1. LiAlH4 C H2C a. b. c. d. CH CH2COOH CH2=CHCH(OH)COOH CH3CH2CH(OH)COOH CH2=CHCH(OH)CH2OH CH3CH2CH(OH)CH2OH 2. H3O+ 10.17 Answer a. b. c. d. CH2=CHCH(OH)COOH CH3CH2CH(OH)COOH CH2=CHCH(OH)CH2OH CH3CH2CH(OH)CH2OH Lithium aluminum hydride reduces ketones and carboxylic acids. 10.18 Identify the compounds that hydrogen and Raney nickel reduces. a. Aldehydes and ketones b. Esters and carboxylic acids c. Aldehydes, ketones, esters, and carboxylic acids d. Alkenes and alkynes e. Aldehydes, ketones, alkenes, and alkynes 10.18 Answer a. Aldehydes and ketones b. Esters and carboxylic acids c. Aldehydes, ketones, esters, and carboxylic acids d. Alkenes and alkynes e. Aldehydes, ketones, alkenes, and alkynes O 10.19 H2C a. b. c. d. Raney Ni C CH CH2COOH CH2=CHCH(OH)COOH CH3CH2CH(OH)COOH CH2=CHCH(OH)CH2OH CH3CH2CH(OH)CH2OH H2 10.19 Answer a. b. c. d. CH2=CHCH(OH)COOH CH3CH2CH(OH)COOH CH2=CHCH(OH)CH2OH CH3CH2CH(OH)CH2OH Hydrogen and Raney nickel reduce ketones and alkenes. 10.20 a. b. c. d. boiling CH3CH2CH2SH CH3CH2CH2SOH CH3CH2CH2SO2H CH3CH2CH2SO3H CH3CH2CH2SO4H HNO3 10.20 Answer a. b. c. d. CH3CH2CH2SOH CH3CH2CH2SO2H CH3CH2CH2SO3H CH3CH2CH2SO4H A thiol is oxidized to a sulfonic acid in the presence of boiling nitric acid.