18.

5 Amides

Tylenol, an aspirin substitute,

contains acetaminophen.
Acetaminophen is an amide;
it acts to reduce fever and
pain; however, it has little
anti-inflammatory effect.

Learning Goal Draw the amide product from amidation, and

give the IUPAC and common names.
General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Preparation of Amides

Amides are derivatives of carboxylic acids in which a

nitrogen group (—NH2) of a primary or secondary amine
replaces the hydroxyl (—OH) group of carboxylic acids.

Core Chemistry Skill Forming Amides

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Preparation of Amides

Amides are produced

• in a reaction called amidation or condensation.
• when a carboxylic acid reacts with ammonia or a primary or
secondary amine and heat.
Amide production is accompanied by the production of water.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Study Check

Predict the products of the following amidation

reaction:

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Solution

Predict the products of the following amidation

reaction:

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Amides

• In both the common and IUPAC names, amides are named by

dropping the oic acid (IUPAC) or ic acid (common) from the
carboxylic acid name and adding the suffix amide.
• Alkyl groups attached to the nitrogen of an amide are named with
the prefix N followed by the alkyl name.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Guide to Naming Amides

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Amides

Give the IUPAC name for the following amide:

ANALYZE Given Need

THE amide IUPAC name
PROBLEM

STEP 1 Replace oic acid (IUPAC) or ic acid common)

in the carboxyl name with amide.

butanamide
General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Naming Amides

Give the IUPAC name for the following amide:

STEP 2 Name each substituent on the N atom using

the prefix N and the alkyl name.

N-methylbutanamide

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Study Check

Give the IUPAC and common names for the following

amides:

A.

B.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Study Check

Give the IUPAC and common names for the following

amides:

ethanamide (IUPAC)
A. acetamide (common)

B.
N-ethylpropanamide (IUPAC)
N-ethylpropionamide (common)

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Physical Properties of Amides

• Amides do not have the properties of bases seen in amines.

• Only methanamide is a liquid at room temperature, while other amides are solids.
• Primary (1°) amides have the highest melting points because the the —NH2 group
can form the most hydrogen bonds.
• Melting points of the secondary (2°) amides are lower because they form fewer
hydrogen bonds.
• Tertiary (3°) amides cannot form hydrogen bonds; they have the lowest melting
points (see Table 18.3).

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 H-Bonding in 1° Amides

Primary (1°) amides, can form

• hydrogen bonds with the –NH2 group of other amides
• hydrogen bonds with water molecules making them soluble
in water as long as they have less than five carbons

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 H-Bonding in 2° Amides

Secondary (2°) amides

• have lower melting points because they form fewer
hydrogen bonds with other amides.
• form hydrogen bonds with water molecules, making them
soluble in water as long as they have fewer than five
carbons.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 H-Bonding in 3° Amides

Tertiary (3°) amides

• have the lowest melting points because they form the
fewest hydrogen bonds.
• can only form one hydrogen bond with H2O.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Chemistry Link to Health:
Amides and Medicine

Urea is
• the simplest natural amide.
• the end product of protein metabolism in the body.
• excreted in the urine.

If the kidneys malfunction, urea is not removed and builds

to a toxic level, a condition called uremia.
General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Chemistry Link to Health:
Amides and Medicine

Aspirin substitutes
• contain phenacetin and acetaminophen.
• act to reduce fever and pain but have little anti-inflammatory
effect.

General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake
 Chemistry Link to Health:
Amides and Medicine

Many barbituates
• are cyclic amides of
barbituric acid.
• act as sedatives in small
doses or sleep inducers in
large doses.
• are habit forming.

Barbiturate drugs include

phenobarbital (Luminal) and
pentobarbital (Nembutal).
General, Organic, and Biological Chemistry: Structures of Life, 5/e © 2016 Pearson Education, Inc.
Karen C. Timberlake