[Maximum number: 1]

Methylamine, $\mathrm{CH}_{3} \mathrm{NH}_{2}$ , has similar chemical properties to ammonia, $\mathrm{NH}_{3}$ . Methylamine reacts with hydrogen chloride to form a white crystalline salt, methylammonium chloride.

\mathrm{CH}_{3} \mathrm{NH}_{2}+\mathrm{HCl} \rightarrow \mathrm{CH}_{3} \mathrm{NH}_{3}^{+} \mathrm{Cl}^{-}

A sample of methylammonium chloride is heated with aqueous sodium hydroxide.
What are the products?

A

ammonia, sodium chloride and water

B

ammonia, sodium hydrogencarbonate and sodium chloride

C

methylamine, hydrogen chloride and water

D

methylamine, sodium chloride and water

[Maximum number: 1]

Methylamine, $\mathrm{CH}_{3} \mathrm{NH}_{2}$ , has very similar chemical properties to ammonia, $\mathrm{NH}_{3}$ .
Methylamine reacts with hydrogen chloride to form a white crystalline salt, methylammonium chloride.

\mathrm{CH}_{3} \mathrm{NH}_{2}+\mathrm{HCl} \rightarrow \mathrm{CH}_{3} \mathrm{NH}_{3}^{+} \mathrm{Cl}^{-}

A sample of methylammonium chloride is heated with aqueous sodium hydroxide.
What are the products?

A

ammonia, sodium chloride and water

B

ammonia, sodium hydrogencarbonate and sodium chloride

C

methylamine, hydrogen chloride and water

D

methylamine, sodium chloride and water

(a)

(i)

Write an equation showing why aqueous solutions of ethylamine are alkaline.

[ 1 ]

[Maximum number: 1]

Coniine is the major constituent of the poison 'oil of hemlock'.

coniine

Coniine can be synthesised by reacting ammonia with a dibromo compound, X.

\begin{gathered} \mathrm{NH}_{3}+\mathrm{C}_{8} \mathrm{H}_{16} \mathrm{Br}_{2} \rightarrow \text { coniine }+2 \mathrm{HBr} \\ \mathbf{X} \end{gathered}

What is the name of compound X ?

A

1,1-dibromo-2-propylcyclopentane

B

1,2-dibromo-2-propylcyclopentane

C

1,4-dibromooctane

D

1,5-dibromooctane

[Maximum number: 1]

The structure of coniine is shown.

Coniine can be synthesised by reacting ammonia with a dibromo compound, X .

\begin{gathered} \mathrm{X} \\ \mathrm{NH}_{3}+\mathrm{C}_{8} \mathrm{H}_{16} \mathrm{Br}_{2} \rightarrow \text { coniine }+2 \mathrm{HBr} \end{gathered}

What is compound X ?

A

1,1-dibromo-2-propylcyclopentane

B

1,2-dibromo-2-propylcyclopentane

C

$\mathrm{Br}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{CHBr}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{CH}_{3}$

D

$\mathrm{Br}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CHBr}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{CH}_{3}$

[Maximum number: 1]

Compounds P, Q and R have all been found in the atmosphere of one of Saturn's moons.
P

Q

R

(a)

The flow chart shows some reactions of R.

R

\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}

[ 1 ]

(i)

T can also be formed by the reaction of $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}$ with ammonia.

State the necessary conditions of this reaction.

[ 1 ]

[Maximum number: 1]

How can a good yield of ethylamine be made using bromoethane as starting material?
1 by heating bromoethane with an excess of ammonia gas in a sealed tube
2 by adding dilute aqueous ammonia to bromoethane at room temperature
3 by heating bromoethane under reflux with aqueous ammonium chloride

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]

How can a good yield of ethylamine be made using bromoethane as starting material?
1 by heating bromoethane with an excess of ammonia gas in a sealed tube
2 by adding dilute aqueous ammonia to bromoethane at room temperature
3 by heating bromoethane under reflux with aqueous ammonium chloride

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: 2]

Ethylamine and phenylamine are primary amines.

Fig. 4.1

These two compounds are synthesised by different methods.

(a)

Several methods can be used to form ethylamine.

[ 2 ]

(i)

Ethylamine forms when ethanamide, $\mathrm{CH}_{3} \mathrm{CONH}_{2}$ , is reduced by $\mathrm{LiAlH}_{4}$ .

Write an equation for this reaction. Use [H] to represent one atom of hydrogen from the reducing agent.

[ 1 ]

(ii)

The reaction in (a)(ii) also forms secondary and tertiary amines.

Suggest the identity of a secondary or tertiary amine formed by the reaction in (a)(ii).

[ 1 ]

(a)

(i)

Explain why ethylamine is basic.

(ii)

Write an equation showing ethylamine acting as
a base,
a nucleophile.