Chemistry

Catherine E. Housecroft, Edwin C. Constable

ISBN #9780273715450

4th Edition

995 Questions

13,222 Students Helped

Homework Questions

Summary

Learning Objectives

Key Concepts

Example Problems

Explanations

Common Mistakes

Summary

This section on amines covers a comprehensive range of topics from their structure and nomenclature to their mechanistic reactions and spectroscopic analysis. It emphasizes the understanding of nitrogen inversion, synthetic routes, and the physical and chemical properties that govern amine behavior. By grasping these concepts, students can predict reactivity patterns and apply these principles in practical organic synthesis and analytical chemistry contexts.

Learning Objectives

Key Concepts

CONCEPT

DEFINITION

Acyclic and cyclic alkanes

A discussion of both open?chain (acyclic) and ring (cyclic) saturated hydrocarbons, emphasizing their structural features, nomenclature, conformational behavior (including ring strain and conformation), and the processes used in their interconversion and synthesis.

Example Problems

Example 1

Give systematic names for the following amines: (FIGURE CANNOT COPY)

Example 2

Draw the structures of the following amines: (a) 2 -hexylamine; (b) 3,3 -dimethyl-l-heptylamine; (c) triethylamine; (d) dimethylamine; (e) 1,4 -butanediamine; (f) isopropylamine; (g) $N, N$ -dimethylbutylamine; (h) 1 -octylamine; (i) benzylamine. Classify each compound as a primary, secondary or tertiary amine.

Example 3

Give structural representations of the following salts: (a) tetraethylammonium chloride; (b) tetrabutylammonium bromide; (c) diethylammonium sulfate; (d) $N, N$ -dimethylbenzylammonium bromide.

Example 4

Explain why racemates of salts of chiral quaternary ammonium ions can usually be resolved whereas this is not generally true for chiral amines in which the chiral centre is the $\mathrm{N}$ atom.

Example 5

(a) Suggest how the reaction of $\mathrm{NH}_{3}$ with 1-bromopropane might proceed. (b) Suggest a method of preparing I-hexylamine in high yield from I -bromohexane.