Organic Chemistry

728 CHAPTER 17 Carbonyl Compounds I

64. Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or
    inorganic reagents.

a. d.

b. e.

c. f.

65. Is the acid-catalyzed hydrolysis of acetamide a reversible or an irreversible reaction? Explain.


66. The reaction of a nitrile with an alcohol in the presence of a strong acid forms a secondary amide. This reaction is known as the
    Ritter reaction. The Ritter reaction does not work with primary alcohols.

a. Propose a mechanism for the Ritter reaction.

b. Why does the Ritter reaction not work with primary alcohols?

c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form a primary amide?

67. The intermediate shown here is formed during the hydroxide-ion-promoted hydrolysis of the ester group. Propose a mechanism for
    the reaction.


68. What product would you expect to obtain from each of the following reactions?

a. b. c.

O

CH 2 CH 2 COH

1. SOCl 2


2. AlCl 3


3. H 2 O

O

CH 2 OH

CH 2 COCH 2 CH 3

HCl

CH 3 CH 2 CHCH 2 CH 2 CH 2 COH

OH O

HCl

CH CH CF 3 CH 2 OH

HO−

CCOCH 2 CF (^3) H 2 O
O
O
N O
CH 3
HC
N O
CH 3
H C
C
C
C
CH 3
N
O +
CH CCO−
O
RC N + R′OH RCNHR′
O
H+
the Ritter reaction
CH 2 COH
O
CH 3
CH 3 (CH 2 ) 10 COH CH 3 (CH 2 ) 11 SO 3 − Na+
O
a detergent
O
NH 2 NH 2
CH 3 C
CH 3 CH 2 CH 2 CH 2 OH CH 3 CH 2 CH 2 CH 2 COH
O
O
CH 3 CNHCH 3
CH 3 CH 2 CNH 2
O
CH 3 CH 2 CCl
O