Chapter 18 Amines and Amides

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

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.

Naming Simple Amines Simple amines are named with common names as alkylamines list the names of the alkyl groups bonded to the N atom in alphabetical order in front of amine Ethylamine Dimethylamine Ethyldimethylamine

Guide to IUPAC Naming of Amines

IUPAC Names of Amines In the IUPAC system, STEP 1 Name the longest carbon chain bonded to the N atoms as alkanamines by replacing e of the alkane name with amine. STEP 2 Number the carbon chain to locate the amine group and any substituents.

Naming Secondary and Tertiary Amines (continued) STEP 3 In a secondary or tertiary amine, use the prefix N- to name groups attached to the N atom.

Learning Check Give the common and IUPAC names, and classify each as primary, secondary, or tertiary. A. CH3—CH2—CH2—NH2 B.

Solution A. STEP 1 Name the longest carbon chain bonded to the N atoms as alkanamines by replacing e of the alkane name with amine. propanamine STEP 2 Number the carbon chain to locate the amine group and any substituents. CH3—CH2—CH2—NH2 3 2 1 Propylamine (common) 1-Propanamine (IUPAC), 1°

Solution (continued) B. STEP 1 Name the longest carbon chain bonded to the N atom as alkanamines by replacing e of the alkane name with amine. ethanamine STEP 2 Number the carbon chain to locate the amine group and any substituents.

Solution (continued) B. STEP 3 In a secondary or tertiary amine, use the prefix N- to name groups attached to the N atom. Ethyldimethylamine (common), N,N-Dimethylethanamine (IUPAC), 3°

Learning Check Draw the condensed structural formula for each of the following: A. 2-pentanamine B. N-methyl-1-butanamine

Solution A. 2-pentanamine B. N-methyl-1-butanamine CH3—CH2—CH2—CH2—NH—CH3

Aromatic Amines The amine of benzene is called aniline may have alkyl groups attached to N that use the prefix N- and the alkyl name Aniline 3-Chloroaniline N-Methylaniline

Learning Check Give the common and IUPAC names for each of the following: A. B. C.

Solution Ethylmethylamine(common); N-methylethanamine A. B. Butylethylmethylamine (common); N-ethyl-N-methyl-1-butanamine C. Aniline