26. Amines

Nitrogenous Nucleophiles

26. Amines

Nitrogenous Nucleophiles

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Four Ways to Make a Primary Amine Precursor

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Four Ways to Make a Primary Amine Precursor

Provide the Major Product

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Textbook Question

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

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Textbook Question

Predict the product(s) of the reactions shown.

b. <IMAGE>

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Textbook Question

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.

<IMAGE>

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Textbook Question

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.

<IMAGE>

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Textbook Question

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

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Textbook Question

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

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(a) <IMAGE>

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Textbook Question

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

(a) 3-ethylbenzoic acid

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Textbook Question

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

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