Organic Chemistry I Problem Set 16 Alcohols and Ethers Practice Exam

I. ____ Multiple Choice. Choose the best answer. 1. a. Which of these dehydrates most easily?
CH3

CH3 CH2 CH2 OH

CH3

b.

OH

c.

OH

d. ____ 2. a.

CH3 C CH2 OH CH3

e.

CH2OH

Which of these is oxidized most easily?

CH3-CHOH-CH 3
CH3

b.

OH

c.

CH3-CH2-O-CH 2-CH3

CH3

d. ____ 3. a. d. ____ 4.

CH3 C CH3 OH

e.

OH

Which of these is a reducing agent? CrO3 / H+ LiAlH4 b. KMnO4 e. O3 ? c. CH4 ?

CH3

c.

H+ / H2O

f. HCOOOH

CH3CH2MgBr + CH3OH b. CH3CH2OCH3

Na2Cr2O7 cool
CH3

a. CH3CH2CH3
CH3

d. CH3CH3

____

5.

CH3 C CH3 OH

a.

CH3 CH3 C CH2

CH3 CH3

b.

CH3 CH CH3

c.

CH3 C CH3 O

d.

CH3 C O C CH3 CH3 CH3

e. No reaction

____

6.

CH2

a. (BH3)2 b. H2O2 / OH-

a.

CH2OH

b.

CH3 OH

c.

d.

OH

____

7.

CH 3 CH 2 O CH 2 CH 3

a. LiAlH4 b. H 2O

a. CH3CH3 ____ 8. a.

b. CH3CH2OH

c. CH3CH2CH2CH3

d. No Reaction

An alcohol of formula C9H12O reacts with Na2Cr2O7 to form a compound with the formula C9H10O. The original alcohol might be.
OH

CH2 CH2 CH2 OH

CH3

b.

CH CH2-CH3

c.

C CH3

OH

d.

CH3 CH CH2OH

____

9. a.

Anisole

excess HI conc reflux

CH2I

b.

+ CH3I

c.

I + CH3OH

d.

OH

+ CH3I

e.

OH

+ CH3CH2I

____

10.

Br2 Fe

Mg ether

ethylene oxide

H+

CrO3/H+ cool

a. d.

benzoic acid phenylacetic acid

b.

acetophenone

c. phenylethyl ether f. styrene oxide

e. styrene

II.

Write the structures of the major products of the following reactions. If no reaction occurs, write N.R. 1.
H2SO 4 heat KMnO4 cold

OH

2.

a. Hg(CH 3COO -)2/H 2O b. NaBH

4

3.

CH3

a. Hg(CF3COO-) 2 / CH3OH b. NaBH4

4.

CH3 CH2 OH

Na

t-butCl

5.

CH3 CH2 CH2 OH

POCl3 heat

CH3COOOH

H+ / H2O

6.

PCC CH2 OH

7.

OH

CrO3 H+ / H2O cool

8.

acetic acid MgBr

9.

CH3 CH2 OH

NaOH

10.

CH3 CH2 OH

NaNH2

11.

CH3 C C CH3 CH2 OH

Na

12.

CH3 CH2 OH

Na

SH

13.

CH3 CH2 OH

NaH

14.

CH3 CH2 OH

CH3COOH H2SO 4, reflux

a. excess CH 3MgI b. H +

15.
MgBr

1. cyclohexanone 2. H3O+

16.

MgBr

1. CH3CH2CHO 2. H3O+

17.
MgBr

1. CO 2 2. H3O+
1. CH3OH 2. H3O+

18.

MgBr

19.

NaBH4 H2O / EtOH

O
20.

CH3 C CH3
O

1. LiAlH 4 2. H2O
1. NaOCH 3 / CH3OH

21.

H2C

CH CH3

2. H2O

22.

CH3 O CH3

1. LiAlH 4 2. H2O

23.

H2C

CH CH3

1. LiAlH 4 2. H2O CH3

24.

CH3 CH2 Br

+ CH3 C O CH3

III.

Answer the following questions: 1. When heated with H2SO4, neopentyl alcohol slowly dehydrates to form 2 alkenes. Show the steps in the mechanism, writing structures for all products of the steps. Be complete!

2.

An optically active compound of formula C9H12O2 produced the following when refluxed with KMnO4.

O HO C

O C OH

The original compound showed these properties as well:

C9H12O2

Na Br2 CrO3 / H+ cool

H2 liberated no rapid reaction C9H8O3

At this point these are at least two possible structures for the original compound. Show one of them.

3.

Using benzene, any straight chain alcohol, and ethylene oxide as sources of carbon, show how you would synthesize these compounds. (Hint Use Grignard rxns.) a.
CH3 CH2 O C CH3 CH3

b.

CH2 C O CH2 CH3

c.

O CH3 CH C CH2