Chapter 18
Amines
CHEM 2124 – General Chemistry II
Alfred State College
Professor Bensley
Learning Objectives
 Identify the characteristics of Amines
 Name Amines
 Give examples of common alkaloids
 Draw the products of acid-base
reactions of amines
 Identify and name ammonium salts
 Discuss the importance of amine
chemistry in the pharmaceutical and
illicit drug businesses.
Amines
I.
Structure and Bonding
A. Introduction
B. Classification
Amines
C. Shape, Bond Angles
D. Physical Properties
1. Odor, Polarity, Hydrogen Bonding, Boiling and
Melting Points
Amines
CH3CH2OCH2CH3
diethyl ether
CH3CH2CH2CH2NH2
1-butanamine
bp = 38 oC
bp = 78 oC
Increasing boiling point
CH3CH2CH2CH2NH2
1-butanamine
CH3CH2CH2CH2OH
1-butanol
bp = 78 oC
bp = 117 oC
Increasing boiling point
Amines
Increasing boiling point
Amines
II. Nomenclature
A. Primary Amines
Systematic
Name:
CH3NH2
CH3CH2CH2CH2NH2
methanamine
1-butanamine
For the common name, name the alkyl group
bonded to the N atom with the suffix “-amine.”
Common Name:
CH3NH2
CH3CH2CH2CH2NH2
methylamine
butylamine
Amines
B. Secondary and Tertiary Amines
1. When the substituents (alkyl groups) are
identical:
2. When substituents (alkyl groups) not
identical:
CH3CHCH3
Example
Name the following
2o amine:
N-methyl-2-propanamine
N H
CH3
Amines
C. Aromatic Rings with N attached
•Reminder: An NH2 group is called an amino group
when named as a substituent.
Amines
III. Interesting Amines (Alkaloids)
Amines
IV. Amines as Bases
Amines
base
acid
conjugate conjugate
acid
base
+ Cl -
Amines
• A water-insoluble amine is converted to a watersoluble ammonium salt by treatment with acid.
water-insoluble
Amines