26. Amines

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

(a) 3-ethylbenzoic acid

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

(b)

Predict the product(s) of the reactions shown.

(b)

Which would you expect to be a stronger nucleophile, ethyl amine or diethyl amine? Why?

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

(a)

The synthesis of ⍺-hydroxy acids can be done starting with amino acids. Suggest a mechanism of the two-step transformation shown. [The alcohol oxygen is the same in the reactant and product.

The final step in the synthesis of diazoxide, a drug used to treat low blood pressure, is shown here. Suggest a mechanism for this step.

Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.

(c) piperidine

Provide a mechanism for the protection of the amine as the benzylcarbamate shown in Figure 26.33(a). <IMAGE>