26. Amines

At the end of a reduction, there was found to be a small amount of unreacted amide along with the amine product dissolved in diethyl ether. How might you remove the amine from the ether?

What are the products of the following reactions?

h.

How can the following compounds be prepared from the given starting materials?

d.

Show how each of the following compounds can be prepared, using the given starting material:

c.

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.

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

Show how you would accomplish the following synthetic conversions.

(c) pentanoic acid → pentan-1-amine

Show how you would accomplish the following synthetic conversions.

(b) 1-bromo-2-phenylethane → 3-phenylpropan-1-amine

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

(d) 4-methoxyaniline

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

(c) 2-methyl-5-hydroxybenzoic acid

Synthesize Novocaine from benzene and any other reagents of four carbons or fewer.

Show how m-toluidine can be converted to the following compounds, using any necessary reagents.

(b)

Show how you would accomplish the following synthetic conversions.

(d) pentanoic acid → hexan-1-amine