Organic Chemistry

718 CHAPTER 17 Carbonyl Compounds I

Tutorial:

Common terms pertaining

to carboxylic acids and

their derivatives

PROBLEM 36

a. Propose a mechanism for the formation of succinic anhydride in the presence of acetic

anhydride.

b. How does acetic anhydride help in the formation of succinic anhydride?

Carbonic acid—a compound with two OH groups bonded to the carbonyl carbon—

is unstable, readily breaking down to and The reaction is reversible, so

carbonic acid is formed when is bubbled into water (Section 1.20).

CO 2 + H 2 O

OH

carbonic acid

HO

C

O

CO 2

CO 2 H 2 O.

HO OH

HO

O

O

succinic anhydride

glutaric anhydride

∆

+ +

O 2 CH 3 OH

acetic anhydride

CH 3 CH 3

O

O

succinic acid

OH

O

O

O

O

C

O

C

O

C

O

O O

P 2 O 5

SYNTHETIC POLYMERS

Synthetic polymers play important roles in our daily

lives. Polymers are compounds that are made by

linking together many small molecules called monomers. In many

synthetic polymers, the monomers are held together by ester and

amide bonds. For example, Dacron is a polyester and nylon is a

polyamide.

®

O

C

O

OCH 2 CH 2 O C OCH 2 CH 2 O

Dacron

n

O

NH(CH 2 ) 5 C

O

NH(CH 2 ) 5 C

O

NH(CH 2 ) 5 C

nylon 6

n

Synthetic polymers have taken the place of metals, fabrics,

glass, ceramics, wood, and paper, allowing us to have a greater

variety and larger quantities of materials than nature could have

provided. New polymers are continually being designed to fit

human needs. For example, Kevlar has a tensile strength

greater than steel. It is used for high-performance skis and bul-

letproof vests. Lexan is a strong and transparent polymer used

for such things as traffic light lenses and compact disks.

®

®

These and other synthetic polymers are discussed in detail in Chapter 28.

O

CO

Lexan

CH 3

CH 3 CH 3

C O

O

CO

CH 3

C O

CH 3

CH 3

C

n

O

C

O

CNH NH

O

C

O

CNH NH

Kevlar

n

3-D Molecules:

Succinic acid;

Succinic anhydride