26. Amines

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:

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Show how m-toluidine can be converted to

the following compounds, using any necessary reagents.

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Using any necessary reagents, show how you would accomplish the following syntheses.

(d) <IMAGE of reaction>

Show how you would use the same sulfonyl chloride as used in the sulfanilamide synthesis to make sulfathiazole and sulfapyridine.

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Predict the products of the following reactions:

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Show how to synthesize the following amines from the indicated starting materials by reductive amination.

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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).

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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 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

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.

(d) cyclohexanone → N-cyclohexylpyrrolidine

What would happen in the synthesis of sulfanilamide if the amino group were not protected as an amide in the chlorosulfonation step?