[Maximum number: 1]

Which row identifies a suitable starting material and reagent that can be used to produce butanenitrile?

starting material

reagent

$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}$

HCN

$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}$

NaCN

$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}$

HCN

$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}$

NaCN

[Maximum number: 1]

Which reagents and conditions would result in the formation of butanenitrile, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CN}$ ?

A

1-bromobutane heated under pressure with ammonia in ethanol

B

1-bromopropane heated with potassium cyanide in ethanol

C

propanal heated with hydrogen cyanide in the presence of potassium cyanide

D

propanone heated with hydrogen cyanide in the presence of potassium cyanide

[Maximum number: 1]

Compound Y is treated with a single reagent under suitable conditions. 2-methylbutanoic acid is produced.

What could compound Y be?

A

pentan-2-one

B

2-methylbutan-2-ol

C

2-methylbutanenitrile

D

methylpropanenitrile

[Maximum number: 1]

In an experiment, $10 \mathrm{~cm}^{3}$ of an organic compound, J, in the gaseous state was sparked with an excess of oxygen. $20 \mathrm{~cm}^{3}$ of carbon dioxide and $5 \mathrm{~cm}^{3}$ of nitrogen were obtained among the products. All gas volumes were measured at the same temperature and pressure.

What could be the identity of J ?
1 $\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{~N}_{2}$
2 $\mathrm{C}_{2} \mathrm{H}_{3} \mathrm{~N}$
3 $\mathrm{C}_{2} \mathrm{H}_{7} \mathrm{~N}$

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

[Maximum number: 1]

Propyl propanoate can be synthesised in three steps using propanenitrile as the only organic starting material.

In step 1, the nitrile is converted into compound X .
In step 2, compound X is converted into compound Y .
In step 3, compound Y is reacted with more of compound X to give propyl propanoate.

Which reagents are suitable for carrying out step 1 and step 2?

step 1

step 2

HCl(aq)

conc. $\mathrm{H}_{2} \mathrm{SO}_{4}$

HCl(aq)

$\mathrm{LiAlH}_{4}$

NaOH(aq)

conc. $\mathrm{H}_{2} \mathrm{SO}_{4}$

NaOH(aq)

$\mathrm{NaBH}_{4}$

[Maximum number: 1]

Which compounds can be used to make Y in a single-step reaction?

1 propanenitrile
2 ethanenitrile
3 propyl ethanoate
4 ethyl propanoate

A

1 and 3

B

1 and 4

C

2 and 3

D

2 and 4

[Maximum number: 1]

Which compound can be used to make propanoic acid by treatment with a single reagent?

A

$\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{CH}_{3}$

B

$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CN}$

C

$\mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{CN}$

D

$\mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{3}$

[Maximum number: 1]

Ethanal reacts with a mixture of HCN and NaCN to make 2-hydroxypropanenitrile, $\mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{CN}$ . The reaction mechanism is nucleophilic addition.

(a)

Give the structure of the organic product of the reaction of $\mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{CN}$ with dilute sulfuric acid.

[ 1 ]

[Maximum number: 1]

Compound $\mathbf{W}, \mathrm{CH}_{2}=\mathrm{CHCN}$ , is used to make an addition polymer which is present in carbon fibres.

(a)

Propanenitrile is heated with hydrogen gas and a platinum catalyst. The only product is propylamine.

Construct an equation for this reaction.

[ 1 ]