Organic Chemistry

840 CHAPTER 19 Carbonyl Compounds III

77. Propose a reasonable mechanism for each of the following reactions:

a.

b.

78. Tyramine is an alkaloid found in mistletoe, ripe cheese, and putrefied animal tissue. Dopamine is a neurotransmitter involved in the
    regulation of the central nervous system.

a. Give two ways to prepare from chloride.

b. How can be prepared from benzyl chloride?

c. How can be prepared from benzaldehyde?

d. How can tyramine be prepared from

e. How can dopamine be prepared from tyramine?

79. Show how estrone, a steroid hormone, can be prepared from the given starting materials. (Hint:Start with a Robinson annulation.)


80. a. Ketoprofen, like ibuprofen, is an anti-inflammatory analgesic. How could ketoprofen be synthesized from the given starting
    material?

b. Ketoprofen and ibuprofen both have a propanoic acid substituent (see Problem 70 in Chapter 17). Explain why the identical

subunits are synthesized in different ways.

OO

CHCOH

CH 3

CH 3

ketoprofen

O

CH 3 OCH 2 CH 2 CH 2 CCH CH 2

+

HO

estrone

O

H 3 C

CH 3 O

O

O HO−

b-phenylethylamine?

b-phenylethylamine

b-phenylethylamine

b-phenylethylamine b-phenylethyl

HO CH 2 CH 2 NH 2 HO

HO

CH 2 CH 2 NH 2

tyramine dopamine

CH 2 Br

OOO

NO 2

OH

+

NO 2

∆

O

O

CCH 3

CH 3 CH 2 O

CH 3 CCH 2 COCH 2 CH 3

O O

1. CH 3 CH 2 O−


2. O
   CH 2 CH 3