1. 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.

2. 10.1 Classify 2,3-dimethyl-2-butanol.
a. 0o alcohol
b. 1o alcohol
c. 2o alcohol
d. 3o alcohol

3. 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.

4. 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

5. 10.2 Answer a. Tert-pentyl alcohol b. Tert-butyl alcohol
c. Isopentyl alcohol
d. Isobutyl alcohol
e. Neopentyl alcohol

6. 10.3 Name a. 1-Butanol b. 2-Butanol c. Butane-1,2-diol
d. Butane-1,2-ol

7. 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.

8. 10.4 Name a. 1-Ethylphenol b. 2-Ethylphenol c. 3-Ethylphenol
d. 4-Ethylphenol

9. 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. 10.5 Give the name of the alcohol that is in beer and wine.
a. Methanol
b. Ethanol
c. 2-Propanol
d. 1-Propanol

11. 10.5 Answer a. Methanol b. Ethanol c. 2-Propanol d. 1-Propanol
The active ingredient in beer and wine is ethanol.

12. 10.6 Give the common use for ethane-1,2-diol.
a. Drinking alcohol
b. Rubbing alcohol
c. Vinegar
d. Antifreeze

13. 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.

14. 10.7 a. NaCH2CH2CH2OH b. CH3CH(Na)CH2OH c. CH3CH2CH(Na)OH
d. CH3CH2CH2ONa

15. 10.7 Answer a. NaCH2CH2CH2OH b. CH3CH(Na)CH2OH c. CH3CH2CH(Na)OH
d. CH3CH2CH2ONa
Sodium reacts with alcohols to form alkoxides.

16. 10.8
a. CH3CH2CH2OH
b. CH3CH2OCH3
c. CH3CH2OH
d. CH3CH2OMgBr

17. 10.8 Answer a. CH3CH2CH2OH b. CH3CH2OCH3 c. CH3CH2OH d. CH3CH2OMgBr
The Grignard reagent adds to the aldehyde to form an alcohol.

18. 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

19. 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.

20. 10.10 a. 3-Methyl-3-pentanol b. 2-Methyl-2-butanol
c. 2-Methyl-3-butanol
d. 2-Methyl-3-pentanol

21. 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.

22. 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

23. 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.

24. 10.12
a. CH3CH2CH(OH)CH3
b. CH3CH2OH
c. CH3CH2CH2OH
d. CH3CH2CH2CH2OH

25. 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.

26. 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.

27. 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.

28. 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

29. 10.14 Answer a. Aldehydes and ketones b. Esters and carboxylic acids
c. Aldehydes, ketones, esters, and carboxylic acids
d. Alkenes and alkynes

30. 10.15 a. CH2=CHCH(OH)COOH b. CH3CH2CH(OH)COOH c. CH2=CHCH(OH)CH2OH
d. CH3CH2CH(OH)CH2OH

31. 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.

32. 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

33. 10.16 Answer a. Aldehydes and ketones b. Esters and carboxylic acids
c. Aldehydes, ketones, esters, and carboxylic acids
d. Alkenes and alkynes

34. 10.17 a. CH2=CHCH(OH)COOH b. CH3CH2CH(OH)COOH c. CH2=CHCH(OH)CH2OH
d. CH3CH2CH(OH)CH2OH

35. 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.

36. 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

37. 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

38. 10.19 a. CH2=CHCH(OH)COOH b. CH3CH2CH(OH)COOH c. CH2=CHCH(OH)CH2OH
d. CH3CH2CH(OH)CH2OH

39. 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.

40. 10.20 a. CH3CH2CH2SOH b. CH3CH2CH2SO2H c. CH3CH2CH2SO3H
d. CH3CH2CH2SO4H

41. 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.