Using any necessary reagents, show how you can accomplish the following multistep syntheses.
(c)

Predict the products of the following reactions:

(d)

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 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 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

Propose a mechanism for the coupling of acetic acid and aniline using DCC as a coupling agent.

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

d.