[Maximum number: 1]

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

piperine

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

(a)

Suggest reagents and conditions for this reaction.

[ 1 ]

[Maximum number: 1]

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

A

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

B

$\mathrm{CH}_{3} \mathrm{CO}_{2}^{-} \mathrm{NH}_{4}^{+}$

C

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

D

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

(a)

(i)

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

[ 1 ]

(ii)

State a reagent for the conversion of butanamide into butylamine.

[ 1 ]

[Maximum number: 1]

The diagram shows the structure of propanamide.

propanamide

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

(a)

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

[ 1 ]

(a)

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

[ 4 ]

[Maximum number: 5]

Neotame is an artificial sweetener added to some foods.

Fig. 8.1

(a)

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

[ 5 ]

(i)

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

1
2

Fig. 8.1

[ 2 ]

(ii)

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

[ 3 ]

[Maximum number: 6]

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

(a)

Fig. 6.1 shows two syntheses starting with glycine.

Fig. 6.1

[ 4 ]

(i)

State the essential conditions for reaction 1.

[ 1 ]

(ii)

Identify the reagent used in reaction 2 .

[ 1 ]

(iii)

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

[ 2 ]

(b)

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

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

[ 2 ]

(i)

Explain why amides are weaker bases than amines.

[ 2 ]