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

Increasing boiling point CH 3 CH 2 OCH 2 CH 3 diethyl ether bp = 38 o C CH 3 CH 2 CH 2 CH 2 NH 2 1-butanamine bp = 78 o C Amines Increasing boiling point CH 3 CH 2 CH 2 CH 2 NH 2 1-butanamine bp = 78 o C CH 3 CH 2 CH 2 CH 2 OH 1-butanol bp = 117 o C

Increasing boiling point Amines

II.Nomenclature A.Primary Amines CH 3 NH 2 methanamine CH 3 CH 2 CH 2 CH 2 NH 2 1-butanamine For the common name, name the alkyl group bonded to the N atom with the suffix “-amine.” CH 3 NH 2 CH 3 CH 2 CH 2 CH 2 NH 2 Common Name: methylaminebutylamine Systematic Name:

Amines B.Secondary and Tertiary Amines 1.When the substituents (alkyl groups) are identical: 2.When substituents (alkyl groups) not identical: Example Name the following 2 o amine: CH 3 CHCH 3 NH CH 3 N-methyl-2-propanamine

Amines C.Aromatic Rings with N attached Reminder: An NH 2 group is called an amino group when named as a substituent.

Amines III.Interesting Amines (Alkaloids)

Amines IV.Amines as Bases

Amines baseacid conjugate acid conjugate base + Cl -

Amines A water-insoluble amine is converted to a water- soluble ammonium salt by treatment with acid. water-insoluble

Amines