Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no more than four carbon atoms as your organic starting materials. Assume that para is the major product (and separable from ortho) in ortho, para mixtures.
(a) pentan-1-amine

Several additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitro compounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds one carbon atom. Show how these amine syntheses can be used for the following conversions.

(c) 1-bromo-3-phenylheptane → 3-phenylheptan-1-amine

Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no more than four carbon atoms as your organic starting materials. Assume that para is the major product (and separable from ortho) in ortho, para mixtures.

(d) N-benzylpropan-1-amine

Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no more than four carbon atoms as your organic starting materials. Assume that para is the major product (and separable from ortho) in ortho, para mixtures.

(b) N-methylbutan-1-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).

Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no more than four carbon atoms as your organic starting materials. Assume that para is the major product (and separable from ortho) in ortho, para mixtures.

(c) N-ethyl-N-propylbutan-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

(a) reductive amination (3 ways).