26. Amines

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

(b)

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

(c) piperidine

Predict the product(s) of the reactions shown.

(b)

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.

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.

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

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

(a)

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

(a) 3-ethylbenzoic acid

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