Lecture 7: Amines and Amides

18.1
Amines

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Amines
Amines
▪ Are derivatives of ammonia NH3.
▪ Contain N attached to one or more alkyl or aromatic
groups.

CH3 CH3
⏐ ⏐
CH3—NH2 CH3—NH CH3—N—CH3

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Classification of Amines
Amines are classified as primary, secondary, or tertiary.
▪ In a primary (1°) amine, one carbon group is bonded
to the nitrogen atom.
▪ A secondary (2°) amine has two carbon groups.
▪ A tertiary (3°) amine has three carbon groups.
H CH3 CH3
| | |
CH3—N—H CH3—N—H CH3—N—CH3
1° 2° 3°

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Models of Amines
The three-dimensional models show the shapes of
amine molecules with one or more alkyl groups
bonded to the nitrogen atom.

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Naming Simple Amines
Simple amines
▪ Are named as alkylamines.
▪ List the names of the alkyl groups bonded to the N
atom in alphabetical order in front of amine.

CH3—CH2—NH2 ethylamine
CH3—NH—CH3 dimethylamine

CH3
|
CH3—N—CH2—CH3 ethyldimethylamine
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IUPAC Names of Amines

In the IUPAC system,

▪ Amines are named as alkanamines.
▪ The e in the alkane name of the longest chain is
changed to amine.
▪ The chain is numbered to locate the amine group
and substituents.
NH2
|
CH3—CH2—NH2 CH3—CH—CH3
Ethanamine 2-Propanamine

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Naming Secondary and Tertiary
Amines
In a secondary or tertiary amine,
▪ The longest alkane chain is numbered.
▪ Each alkyl group bonded to the N atom is named as a
N-alkyl group
HN—CH3
|
CH3—CH2—CH2—NH—CH3 CH3—CH—CH2—CH3
3 2 1 1 2 3 4

N-Methyl-1-propanamine N-Methyl-2-butanamine

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Learning Check

Give the common and IUPAC names, and classify as

primary, secondary, or tertiary:
A. CH3—CH2—CH2—NH2

CH3
|
B. CH3—CH2—N—CH3

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Learning Check
Write a structural formula for
A. 2-pentanamine

B. N-methyl-1-butanamine

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Aromatic Amines
▪ The amine of benzene is aniline.
▪ Alkyl groups on the N use the prefix N- and the alkyl
name.

Aniline 3-chloroaniline N-methylaniline

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Learning Check
Give a name for each:
A. CH3—NH—CH2—CH3

CH3
|
B. CH3—CH2—N—CH2—CH2—CH2—CH3

C.

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Solution
A. CH3—NH—CH2—CH3
ethylmethylamine; N-methylethanamine

CH3
|
B. CH3—CH2—N—CH2—CH2—CH2—CH3

N-ethyl-N-methyl-1-butanamine

C. aniline

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Learning Check

Consider the following compounds:

1. CH3—CH2—CH2—NH2
2. CH3—CH2—NH—CH3
3. CH3—CH2—CH2—CH3

A. Which compound has the highest boiling point?

B. Which compound(s) is(are) soluble in water?

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Solution
Consider the following compounds:
1. CH3—CH2—CH2—NH2
2. CH3—CH2—NH—CH3
3. CH3—CH2—CH2—CH3

A. Which compound has the highest boiling point?

1. CH3—CH2—CH2—NH2

B. Which compound(s) is(are) soluble in water?

1. CH3—CH2—CH2—NH2
2. CH3—CH2—NH—CH3

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Cocaine
Cocaine
▪ Is sold illegally as an amine salt.
▪ Is reacted with NaOH to produce the free amine form
known as “crack”.

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Lecture 7: Amines and Amides
18.3
Heterocyclic Amines and Alkaloids

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Heterocyclic Amines
A heterocyclic amine
▪ Is a cyclic organic compound.
▪ Has a five- or six-atom ring.
▪ Contains one or more nitrogen atoms.

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Examples of Heterocyclic Amines

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Learning Check
Identify the following heterocyclic amines:
1. 2. 3.

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Solution
Identify the following heterocyclic amines:
1. 2. 3.

1. piperidine 2. pyrrole 3. imidazole

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Alkaloids

Alkaloids are
▪ Physiologically active nitrogen-containing
compounds.
▪ Produced by plants.
▪ Used as stimulants, anesthetics, and
antidepressants.
▪ Often habit forming.

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Caffeine
Caffeine
▪ Is a stimulant of the
central nervous system.
▪ Is found in coffee
beans, tea, chocolate,
and soft drinks.
▪ Contains an imidazole
ring.

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Nicotine

Nicotine
▪ Increases the adrenaline level in the blood.
▪ Causes addiction to tobacco.
▪ Contains a pyrrolidine ring.

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Alkaloids Related to Morphine

Alkaloids
▪ Such as morphine and codeine are produced by the
poppy.
▪ Have been used for centuries as painkillers.
▪ Such as heroin and codeine are modifications of
morphine.

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Morphine and Codeine

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 Pharmacology

An area of research in pharmacology

▪ Is to design drugs such as procaine, lidocaine, and
demerol that retain some of the characteristics of
alkaloids.
▪ Is to modify the structures of cocaine and morphine
to produce anesthesia, but without the addictive
side effects.

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Pharmacology

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Learning Check
Identify the heterocyclic amine in serotonin.

serotonin

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Solution
Identify the heterocyclic amine in serotonin.

pyrrole

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Lecture 7: Amines and Amides

18.4
Amides

Copyright © 2007 by Pearson Education, Inc.

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Preparation of Amides
Amides are prepared
▪ By reacting a carboxylic acid with ammonia or
an amine (1° or 2°).
▪ Using heat.
O O
|| Heat ||
CH3—C—OH + NH3 CH3—C—NH2 + H2O

O O
|| Heat ||
CH3—C—OH + CH3—NH2 CH3—C—NH—CH3 + H2O

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Amides
In amides, an amino group(–NH2) replaces the –OH
group of carboxylic acids.
O O
|| ||
CH3—C—OH CH3—C—NH2

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Naming Amides

Amides are named as alkanamides.

▪ IUPAC replaces –oic acid ending with –amide.
▪ Common names replace -ic acid ending with –amide.
O
|| Methanamide (IUPAC)
H—C—NH2 Formamide (common)

O
|| Propanamide (IUPAC)
CH3—CH2—C—NH2 Propionamide (common)

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 Naming Amides with N Groups

▪ An alkyl group bonded to the N atom is named as

N-alkyl in front of the amide name.
O H
|| │
CH3 —C—N—CH3 N-methylethanamide (IUPAC)
N-methylacetamide (common)
O H
|| │
CH3—CH2 —C—N—CH2—CH3
N-ethylpropanamide (IUPAC)
N-ethylpropionamide (common)

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Aromatic Amides

▪ The amide of benzene is named benzamide.

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 Learning Check
Give the IUPAC and common names for the following:

O
||
A. CH3–CH2–CH2–C–NH2

O H
|| │
B. CH3–C–N–CH2–CH3

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Solution
O
||
A. CH3–CH2–CH2–C–NH2
butanamide; butryamide

OH
|| │
B. CH3–C–N–CH2–CH3

N-ethylethanamide; N-ethylacetamide

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Learning Check

Draw the structures of

A. pentanamide
B. N-methylbutyramide

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Solution

A. pentanamide
O
||
CH3–CH2–CH2–CH2–C–NH2

B. N-methylbutyramide
O
||
CH3–CH2–CH2–C–NH–CH3

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Classification of Amides
▪ Amides are classified according to the number of
carbon atoms bonded to the nitrogen atom.
O H
|| |
CH3—C—N—H Primary (1°) amide

O H
|| |
CH3—C—N—CH3 Secondary (2°) amide

O CH3
|| |
CH3 —C—N—CH3 Tertiary (3°) amide

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 Learning Check

Give the common and IUPAC names for the following

amides and classify as primary, secondary, or tertiary:

O
||
A. CH3—CH2—CH2—C—NH2

O CH3
|| |
B. CH3—C—N—CH2—CH3

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Solution

O
||
A. CH3—CH2—CH2—C—NH2
butryamide (common);
butanamide (IUPAC) primary(1°) amide

O CH3
|| |
B. CH3—C—N—CH2—CH3
N-ethyl-N-methylacetamide (common);
N-ethyl-N-methylethanamide (IUPAC)
tertiary (3°) amide

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Some Amides in Health and
Medicine
▪ Urea is the end product of protein metabolism.
▪ Saccharin is an artificial sweetener.
▪ Some amides such as phenobarbital, Nembutal
and Seconal are barbiturates.
▪ Acetaminophen is used to reduce fever and
pain.

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 Some Amides in Health and Medicine

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Physical Properties of Amides
Amides
▪ That are primary (−NH2) or secondary (−NH−) form
hydrogen bonds.
▪ That are primary have higher melting points than
secondary.
▪ That are tertiary (no H on N) do not form hydrogen
bonds and have lower melting points.
▪ All form hydrogen bonds with water.
▪ With 1-5 carbon atoms are soluble in water.

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