Page 283 - Theory and Problems of BEGINNING CHEMISTRY

272 ORGANIC CHEMISTRY [CHAP. 18

fats are converted to soaps (fatty acid salts) and glycerine (a trialcohol) in this manner.

CH OH CH OCOC H 35
2
2
17
3 C H CO H + CHOH CHOCOC H 35 + 3 H O
2
17
35
17
2
fatty acid
CH 2 OH CH 2 OCOC 17 H 35
+ glycerine animal fat
3 NaOH
+ −
3 Na C H CO 2 + 3 H 2 O
17
35
a soap
Nitroglycerine, a powerful explosive, is an ester of the inorganic acid HNO 3 and glycerol (glycerine).
H C OH H C O NO 2
2
2
HC OH + 3 HNO 3 3 H O + HC O NO 2
2
H SO 4
2
H C OH H C O NO 2
2
2
glycerine nitroglycerine
18.11. AMINES
Amines can be considered derivatives of ammonia, NH 3 , in which one or more hydrogen atoms have been
replaced by organic radicals. For example, replacing one hydrogen atom on the nitrogen atom results in a primary
amine, RNH 2 .A secondary amine has a formula of the type R 2 NH, and a tertiary amine has the formula R 3 N.
Like ammonia, amines react as Brønsted bases:

+
−→
RNH 2 + H 2 O ←− RNH 3 + OH −
Aromatic amines are of considerable importance commercially. The simplest aromatic amine, aniline,
C 6 H 5 NH 2 , is used in the production of various dyes and chemicals for color photography.

18.12. AMIDES
This class of compounds is formed by the reaction of organic acids with amines. The functional group and
the general formula are

C N R C N R′
O O R′′

Any or all of the R groups can be the same or different, and indeed may even be a hydrogen atom. The simplest
amide is formamide, HCONH 2 . The name of each member of the group starts with any radicals attached to the
nitrogen atom. Then comes the name of the organic acid, with -oic acid replaced by the word amide.

CH 3 C OH + HN(CH ) CH 3 C N(CH ) + H O
3 2
3 2
2
dimethylamine
O O
acetic acid or dimethyl acetamide or
ethanoic acid dimethyl ethanamide
Amino acids form proteins in the human body with amide linkages, and the same linkages hold together the
building blocks of nylon.