Amides (Cambridge (CIE) A Level Chemistry): Exam Questions

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

Fig. 1.1

i) Draw the skeletal formulae of compounds A and B in the boxes in Fig. 1.1.

[2]

ii) State the reagents and conditions for step 1 in the box over the arrow in Fig. 1.1.

[2]

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

i) State the name of the functional group formed in this reaction.

[1]

ii) Calculate the percentage by mass of nitrogen in C.

[1]

iii) Draw the structural formula of C.

[1]

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

Fig. 1.2

i) State which of these two compounds is the weaker base. Explain your answer.

[3]

ii) State the name or formula of a suitable reducing agent for this reduction.

[1]

When benzamide is refluxed with dilute acid, hydrolysis occurs.

i) Draw the skeletal formula of the organic product formed.

[1]

ii) State the name of the other product formed during this hydrolysis reaction.

[1]

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

Fig. 2.1

i) State the reagents and conditions required to produce N-ethylethanamide.

[2]

ii) State the type of reaction that occurs during the formation of N-ethylethanamide.

[1]

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

State the relative order of basicity of diethylamine, N-ethylethanamide and ammonia in aqueous solution. Explain your reasoning.

least basic ......................... > ......................... > ......................... most basic

Methylamine reacts with propanoyl chloride to form CH₃CH₂CONHCH₃.

i) State the name of the mechanism for this reaction.

[1]

An incomplete mechanism for this reaction is shown in Fig. 3.1.

Fig. 3.1

ii) Complete the mechanism in Fig. 3.1. Include all relevant curly arrows, lone pairs, and dipoles. Also show the formula of the second product formed.

[5]

State the systematic name of the organic product formed in part (a).

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

i) State the role of LiAlH₄ in this reaction.

[1]

ii) State the name of the other product formed during this reaction.

[1]