Organic Chemistry, 7e by L. G. Wade, Jr.

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Presentation transcript:

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-2-butanol. a. 0o alcohol b. 1o alcohol c. 2o alcohol d. 3o alcohol

10.1 Answer a. 0o alcohol b. 1o alcohol c. 2o alcohol d. 3o alcohol The carbon bearing the –OH has three other carbons attached to it.

10.2 Give the common name for (CH3)3CCH2OH. a. Tert-pentyl alcohol b. Tert-butyl alcohol c. Isopentyl alcohol d. Isobutyl alcohol e. Neopentyl alcohol

10.2 Answer a. Tert-pentyl alcohol b. Tert-butyl alcohol c. Isopentyl alcohol d. Isobutyl alcohol e. Neopentyl alcohol

10.3 Name a. 1-Butanol b. 2-Butanol c. Butane-1,2-diol d. Butane-1,2-ol

10.3 Answer a. 1-Butanol b. 2-Butanol c. Butane-1,2-diol d. Butane-1,2-ol Butane is the longest chain; the OHs are in the 1 and 2 positions.

10.4 Name a. 1-Ethylphenol b. 2-Ethylphenol c. 3-Ethylphenol d. 4-Ethylphenol

10.4 Answer a. 1-Ethylphenol b. 2-Ethylphenol c. 3-Ethylphenol d. 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. Methanol b. Ethanol c. 2-Propanol d. 1-Propanol

10.5 Answer a. Methanol b. Ethanol c. 2-Propanol d. 1-Propanol The active ingredient in beer and wine is ethanol.

10.6 Give the common use for ethane-1,2-diol. a. Drinking alcohol b. Rubbing alcohol c. Vinegar d. Antifreeze

10.6 Answer a. Drinking alcohol b. Rubbing alcohol c. Vinegar d. Antifreeze Ethane-1,2-diol (ethylene glycol) is used as antifreeze; it is very toxic to animals.

10.7 a. NaCH2CH2CH2OH b. CH3CH(Na)CH2OH c. CH3CH2CH(Na)OH d. CH3CH2CH2ONa

10.7 Answer a. NaCH2CH2CH2OH b. CH3CH(Na)CH2OH c. CH3CH2CH(Na)OH d. CH3CH2CH2ONa Sodium reacts with alcohols to form alkoxides.

10.8 a. CH3CH2CH2OH b. CH3CH2OCH3 c. CH3CH2OH d. CH3CH2OMgBr

10.8 Answer a. CH3CH2CH2OH b. CH3CH2OCH3 c. CH3CH2OH d. 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. 0o alcohol b. 1o alcohol c. 2o alcohol d. 3o alcohol

10.9 Answer a. 0o alcohol b. 1o alcohol c. 2o alcohol d. 3o alcohol A Grignard reagent adds to a ketone to give, after hydrolysis, a 3o alcohol.

10.10 a. 3-Methyl-3-pentanol b. 2-Methyl-2-butanol c. 2-Methyl-3-butanol d. 2-Methyl-3-pentanol

10.10 Answer a. 3-Methyl-3-pentanol b. 2-Methyl-2-butanol c. 2-Methyl-3-butanol d. 2-Methyl-3-pentanol Two methyls add to the carbonyl carbon, followed by hydrolysis.

10.11 a. 3-Methyl-3-pentanol + methanol b. 2-Methyl-2-butanol + ethanol c. 2-Methyl-3-butanol + methanol d. 2-Methyl-3-pentanol + ethanol

10.11 Answer a. 3-Methyl-3-pentanol + methanol b. 2-Methyl-2-butanol + ethanol c. 2-Methyl-3-butanol + methanol d. 2-Methyl-3-pentanol + ethanol Two methyls add to the carbonyl carbon, followed by hydrolysis. The ethoxide is protonated.

10.12 a. CH3CH2CH(OH)CH3 b. CH3CH2OH c. CH3CH2CH2OH d. CH3CH2CH2CH2OH

10.12 Answer a. CH3CH2CH(OH)CH3 b. CH3CH2OH c. CH3CH2CH2OH d. 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

10.15 a. CH2=CHCH(OH)COOH b. CH3CH2CH(OH)COOH c. CH2=CHCH(OH)CH2OH d. CH3CH2CH(OH)CH2OH

10.15 Answer a. CH2=CHCH(OH)COOH b. CH3CH2CH(OH)COOH c. CH2=CHCH(OH)CH2OH d. 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

10.17 a. CH2=CHCH(OH)COOH b. CH3CH2CH(OH)COOH c. CH2=CHCH(OH)CH2OH d. CH3CH2CH(OH)CH2OH

10.17 Answer a. CH2=CHCH(OH)COOH b. CH3CH2CH(OH)COOH c. CH2=CHCH(OH)CH2OH d. 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

10.19 a. CH2=CHCH(OH)COOH b. CH3CH2CH(OH)COOH c. CH2=CHCH(OH)CH2OH d. CH3CH2CH(OH)CH2OH

10.19 Answer a. CH2=CHCH(OH)COOH b. CH3CH2CH(OH)COOH c. CH2=CHCH(OH)CH2OH d. CH3CH2CH(OH)CH2OH Hydrogen and Raney nickel reduce ketones and alkenes.

10.20 a. CH3CH2CH2SOH b. CH3CH2CH2SO2H c. CH3CH2CH2SO3H d. CH3CH2CH2SO4H

10.20 Answer a. CH3CH2CH2SOH b. CH3CH2CH2SO2H c. CH3CH2CH2SO3H d. CH3CH2CH2SO4H A thiol is oxidized to a sulfonic acid in the presence of boiling nitric acid.