Reduction of two different carboxylic acid derivatives with LiAlH₄ would give the amine shown. Identify these carboxylic acid derivatives.

Show how you would accomplish the following synthetic conversions.

(d) pentanoic acid → hexan-1-amine

Show how you would accomplish the following synthetic conversions.

(e) (R)-2-bromobutane → (S)-butan-2-amine

Show how you can synthesize the following tertiary amine three different ways, each using a different secondary amine and adding the final substituent by (b) acylation–reduction (3 ways).

The two most general amine syntheses are the reductive amination of carbonyl compounds and the reduction of amides. Show how these techniques can be used to accomplish the following syntheses.

(a) benzoic acid → benzylamine

Predict the product of the following reaction sequences.

(b)

Give the expected products of lithium aluminum hydride reduction of the following compounds (followed by hydrolysis).

(a) butyronitrile

(b) N-cyclohexylacetamide

(c) ε-caprolactam

Predict the products of the following reactions.

(e)

(f)

Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.

(a) hexan-1-ol → heptan-1-amine