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A LevelChemistryCIEExam Questions34. Nitrogen Compounds (AL)34.3 Amides

Amides (CIE A Level Chemistry)

Exam Questions

29 mins4 questions
Easy
Medium
1a1 mark

Amides can be formed from amines. An example is shown in the following reaction scheme where compound X reacts with methylamine to form N-methyl propanamide and hydrogen chloride.


compound X + CH3NH2 → CH3CH2CONHCH3 + HCl

State the structural formula of compound X.

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1b1 mark

N-methyl propanamide can undergo reduction forming compound Y and water. State the reagent required for this reaction.

Reagent .................................................................

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1c1 mark

A different amide, ethanamide was heated with sodium hydroxide the gas ammonia is formed along with one other product.

i)
Write the equation for this reaction.
[1]
ii)
Explain how this reaction could be used as a test for an amide.
[2]

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1a4 marks

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

7-6-4a-m-reactions-of-phenylamine-a

Fig. 1.1

i)
Suggest the structural formulae of A and B in the boxes in Fig. 1.1.

[2]

ii)
Suggest suitable reagents and conditions for step 1, and write them in the box over the arrow in Fig. 1.1.

[2]

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1b
Sme Calculator3 marks

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

i)
Name the functional group formed in this reaction.

[1]

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

[1]

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

iii)
Draw the structural formula of C.

[1]

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1c4 marks

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

imKScUyS_benzamide-and-benzylamine

Fig. 1.2

i)
State which is the weaker base, benzamide or benzylamine. Explain your answer.

[3]

ii)
Give a suitable reducing agent required for this reduction.

[1]

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1d2 marks

When benzamide is refluxed with acid, hydrolysis occurs.

i)
Draw the structural formula of the resulting organic compound.

[1]

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

[1]

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2a1 mark

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

n-ethylethanamide

Fig. 2.1

i)
Give the reactants and conditions to produce N-ethyl ethanamide.
[1]
ii)
State the type of reaction that occurs during the formation of N-ethylethanamide.
[1]

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2b1 mark

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

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2c3 marks

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

Explain your reasoning.

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

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3a6 marks

Methylamine reacts with propanoyl chloride to form CH3CH2CONHCH3.

i)
Name the mechanism for this reaction.
[1]
 

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

AoNZHBMy_methylamine-and-propanoyl-chloride-mechanism-fill

Fig. 3.1

ii)
Complete the mechanism in Fig. 3.1. You should include:
  • 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.
[4]

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3b1 mark

Name the organic product of part (a).

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3c1 mark

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

i)
State the role of the LiAlH4.
[1]
 
ii)
Give the name of the other chemical formed during this reaction.
[1]

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