Organic Chemistry

676 CHAPTER 17 Carbonyl Compounds I

PROBLEM 2

Name the following compounds:

a. d. g.

b. e. h.

c. f. i.

PROBLEM 3

Write a structure for each of the following compounds:

a. phenyl acetate d.N-benzylethanamide g.

b. e. acid h. propanoic anhydride

c. butanenitrile f. ethyl 2-chloropentanoate i. cyclohexanecarbonyl

chloride

17.2 Structures of Carboxylic Acids

and Carboxylic Acid Derivatives

The carbonyl carbonin carboxylic acids and carboxylic acid derivatives is hy-

bridized. It uses its three orbitals to form bonds to the carbonyl oxygen, the

and a substituent (Y). The three atoms attached to the carbonyl carbon are in

the same plane, and their bond angles are each approximately 120°.

The carbonyl oxygenis also hybridized. One of its orbitals forms a bond

with the carbonyl carbon, and each of the other two orbitals contains a lone pair.

The remaining porbital of the carbonyl oxygen overlaps with the remaining porbital

of the carbonyl carbon to form a bond (Figure 17.1).p

sp^2

sp^2 sp^2 s

O

C

Y

~120° ~120°

~120°

a-carbon,

sp^2 s

sp^2

g-caprolactam g-caproic

b-bromobutyramide

CH 3

O

O

O

CH 3 CH 2 CH 2 CH 2 CH 2 CN(CH 3 ) 2

O

CH 3 CH 2 CH 2 CO−^ K+

COOH

O CH 3

CH 3 CH 2 CH 2 COCH 2 CHCH 3

O O

CH 3 CH 2 COCCH 3

O

NH

O

CH 3 CH 2 CH 2 C‚N CH 3 CH 2 CH 2 CH 2 CCl

bond C O

bond

Figure 17.1N
Bonding in a carbonyl group.
The bond is formed by side-to-
side overlap of a porbital of carbon
with a porbital of oxygen.

p

3-D Molecules:

Acetyl chloride;

Methyl acetate;

Acetic acid; Acetamide