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A-Level CAIE Chemistry A234.3 AmidesQuestion Bank

34.3 Amides

Question 3

Question 3(c)

(a)

The hydrolysis of compound F produces two compounds G and H.

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[ 3 ]

Question 3(c)(i)

(i)

State the reagents and conditions needed for this hydrolysis.

Question 3(c)(ii)

(ii)

Draw the structures of the two products G and H in the boxes above.

[ 3 ]

Question 3

[Maximum number: 1]

Piperine is the compound responsible for the hot taste of black pepper.

piperine

piperine

Piperine is an amide and can be broken down as follows:

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Question 3(a)

(a)

Suggest reagents and conditions for this reaction.

[ 1 ]

Question 30

[Maximum number: 1]

What is the organic product when ethanamide, CH3CONH2\mathrm{CH}_{3} \mathrm{CONH}_{2}, is boiled with excess aqueous sodium hydroxide?

A

CH3CN\mathrm{CH}_{3} \mathrm{CN}

B

CH3CO2−NH4+\mathrm{CH}_{3} \mathrm{CO}_{2}^{-} \mathrm{NH}_{4}^{+}

C

CH3CONH−Na+\mathrm{CH}_{3} \mathrm{CONH}^{-} \mathrm{Na}^{+}

D

CH3CO2−Na+\mathrm{CH}_{3} \mathrm{CO}_{2}{ }^{-} \mathrm{Na}^{+}

Question 4

Question 4(b)

Question 4(b)(iii)

(a)
(i)

State how the basicity of butanamide, C3H7CONH2\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{CONH}_{2}, compares to that of butylamine.

[ 1 ]

Question 4(b)(iv)

(ii)

State a reagent for the conversion of butanamide into butylamine.

[ 1 ]

Question 40

[Maximum number: 1]

The diagram shows the structure of propanamide.

propanamide

propanamide

Which statements about the hydrolysis of propanamide are correct?
1 Propanamide can be hydrolysed by heating under reflux with H2SO4(aq)\mathrm{H}_{2} \mathrm{SO}_{4}(\mathrm{aq}).
2 Propanamide can be hydrolysed by heating under reflux with NaOH(aq).
3 Propanamide can be hydrolysed by cold water.

A

1, 2 and 3 are correct

B

1 and 2 only are correct

C

2 and 3 only are correct

D

1 only is correct

Question 8

Question 8(c)

(a)

Explain why benzamide, C6H5CONH2\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CONH}_{2}, is a much weaker base than ammonia, NH3\mathrm{NH}_{3}.

[ 1 ]

Question 7

Question 7(a)

(a)

State the relative basicities of ethanamide, diethylamine and ethylamine in aqueous solution.
Explain your answer. > >
most basic
least basic

[ 4 ]

Question 8

[Maximum number: 5]

Neotame is an artificial sweetener added to some foods.

Fig. 8.1

Fig. 8.1

Question 8(b)

(a)

Neotame reacts with an excess of hot NaOH(aq) to form three organic products.

[ 5 ]

Question 8(b)(i)

(i)

State the two types of reaction that occur when neotame reacts with hot NaOH(aq).

1
2

Fig. 8.1

Fig. 8.1

[ 2 ]

Question 8(b)(ii)

(ii)

Draw the structures of the three organic products formed from the reaction of neotame with an excess of hot NaOH(aq).

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[ 3 ]

Question 6

[Maximum number: 6]

Amino acids are molecules that contain −NH2-\mathrm{NH}_{2} and -COOH functional groups.
Glycine, H2NCH2COOH\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{COOH}, is the simplest stable amino acid.

Question 6(b)

(a)

Fig. 6.1 shows two syntheses starting with glycine.

Fig. 6.1

Fig. 6.1

[ 4 ]

Question 6(b)(i)

(i)

State the essential conditions for reaction 1.

[ 1 ]

Question 6(b)(ii)

(ii)

Identify the reagent used in reaction 2 .

[ 1 ]

Question 6(b)(iii)

(iii)

Draw the structure of the organic product U that forms when hippuric acid reacts with an excess of LiAlH4\mathrm{LiAlH}_{4} in reaction 3 .

[ 2 ]

Question 6(c)

(b)

A student proposes a synthesis of hippuric acid by the reaction of benzamide, C6H5CONH2\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CONH}_{2}, and chloroethanoic acid, ClCH2COOH\mathrm{ClCH}_{2} \mathrm{COOH}.

The reaction does not work well because benzamide is a very weak base.

[ 2 ]

Question 6(c)(i)

(i)

Explain why amides are weaker bases than amines.

[ 2 ]
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