Chapter 18, Problem 18.97P

Interpretation Introduction

Interpretation:

It is to be shown how to synthesize $\text{2, 3-dimethylpentan-1-amine}$ using only compounds containing three or fewer carbon atoms.

Concept introduction:

Amines can be prepared from the corresponding imines using a reducing agent such as ${\text{NaBH}}_4$. Imines are prepared from the nucleophilic addition reaction of an aldehyde and ammonia. An alkyl group can be incorporated into a beta position of an alpha-beta unsaturated carbonyl compound using Gilman reagent via conjugate addition. Alpha-beta unsaturated carbonyl compounds are synthesized from an aldol condensation reaction. A retrosynthetic approach is useful in planning a synthesis of the target molecule using the given starting molecule and any other reagents.