26. Amines

Synthesize from benzene. (Hint: All of these require diazonium ions.)

(c) 2-methyl-5-hydroxybenzoic acid

Predict the products of the following reactions.

(e)

(f)

Show how you would accomplish the following synthetic conversions.

(f) (R)-2-bromobutane → (S)-2-methylbutan-1-amine

Predict the product of the following reaction sequences.

(b)

Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene and toluene as your aromatic starting materials.

(d) m-aminobenzoic acid

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.

(c) pyrrolidine → N-ethylpyrrolidine

Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene and toluene as your aromatic starting materials.

(a) aniline

Show how you would accomplish the following synthetic conversions.

(a) benzyl bromide → benzylamine