Amides (CIE A Level Chemistry)

Phenylamine can be converted into the organic compounds A and B as shown in Fig. 1.1.

Fig. 1.1

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When phenylamine is treated with propanoyl chloride a white crystalline compound, C, C₉H₁₁NO, is formed.

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percentage = ........................ %

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Fig. 1.2 shows the reduction of benzamide to form benzylamine.

Fig. 1.2

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When benzamide is refluxed with acid, hydrolysis occurs.

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The structure of N-ethylethanamide is shown in Fig. 2.1.

Fig. 2.1

Write an equation to show the alkaline hydrolysis of N-ethylethanamide.

Describe the relative basicities of diethylamine, N-ethylethanamide and ammonia in aqueous solution.

Explain your reasoning.

Methylamine reacts with propanoyl chloride to form CH₃CH₂CONHCH₃.

An incomplete description of the mechanism of this reaction is shown in Fig. 3.1.

Fig. 3.1

• all relevant dipoles (δ+ and δ–) and full electric charges (+ and –) on the reactants and intermediate
• all relevant lone pairs on the reactants and intermediate 
• all relevant curly arrows to show the movement of electron pairs on the reactants and intermediate
• the formula of the second product.

Name the organic product of part (a).

The organic product of part (a) reacts with LiAlH₄ to form a secondary amine.