[Maximum number: 1]

Species such as $\mathrm{NH}_{4}{ }^{+}, \mathrm{CO}_{3}{ }^{2-}$ and $\mathrm{PO}_{4}{ }^{3-}$ are examples of molecular ions.

(a)

$\mathrm{OH}^{-}(\mathrm{aq})$ reacts with 2-bromo-2-methylpropane in an $\mathrm{S}_{\mathrm{N}} 1$ reaction. The molecular ion $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}^{+}$ forms as the intermediate in this reaction.

[ 1 ]

(i)

Organic compound M forms when 2-bromo-2-methylpropane is heated with ethanolic $\mathrm{OH}^{-}$ .

Draw the structure of M.

[ 1 ]

[Maximum number: 5]

Hydrogen iodide, HI, is a colourless gas at room temperature.

(a)

HI(g) reacts with propene, $\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}(\mathrm{~g})$ to form a mixture of 1-iodopropane and 2-iodopropane.

[ 5 ]

(i)

Identify which of 1-iodopropane and 2-iodopropane is the major product of this reaction.

Explain your answer.

[ 2 ]

(ii)

Complete the diagram to show the mechanism of the reaction between HI and $\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}$ that forms the major product identified in (g)(i).

Include curly arrows, lone pairs of electrons and charges as necessary.

[ 3 ]

[Maximum number: 3]

Nitrogen, $\mathrm{N}_{2}$ , is the most abundant gas in the Earth's atmosphere and is very unreactive.

(a)

Nitrosyl chloride, NOCl , is a reactive gas that is sometimes formed when NO reacts with $\mathrm{Cl}_{2}$ .

NOCl is a strong electrophile and readily undergoes an addition reaction with alkenes.
Complete the diagram to show the mechanism of the electrophilic addition reaction of NOCl with ethene.

Include all necessary charges, lone pairs and curly arrows, and the structure of the organic intermediate.

[ 3 ]

(a)

Another hydrocarbon, W, with the formula $\mathrm{C}_{4} \mathrm{H}_{8}$ , reacts with hydrogen bromide, HBr , to give two products X and Y. X and Y are structural isomers of molecular formula $\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{Br}$ .

Reaction of X with aqueous alkali produces an alcohol, Z, that has no reaction with acidified dichromate(VI).

[ 2 ]

(i)

When W reacts with hydrogen bromide, more X than Y is produced. Explain why.

[ 2 ]

[Maximum number: 5]

Elements and compounds which have small molecules usually exist as gases or liquids.

(a)

HCN reacts with ethanal, $\mathrm{CH}_{3} \mathrm{CHO}$ .

[ 5 ]

(i)

Give the displayed formula of the organic product formed.

(ii)

Draw the mechanism of this reaction. You should show all full and partial charges and represent the movement of electron pairs by curly arrows.

[ 5 ]

[Maximum number: 2]

Carbon and silicon are elements in Group 14.

(a)

$\mathrm{C}_{60}$ forms hydrocarbons with similar chemical properties to those of alkenes. One such hydrocarbon is $\mathrm{C}_{60} \mathrm{H}_{18}$ .

[ 2 ]

(i)

Describe a test to indicate the presence of double bonds between carbon atoms in $\mathrm{C}_{60} \mathrm{H}_{18}$ . Give the result of the test.
test
result

[ 2 ]

[Maximum number: 1]

This question should be answered by considering the reactions of $\mathrm{KMnO}_{4}$ with different functional groups under the stated conditions.

The diagram shows the structure of the naturally-occurring molecule cholesterol.

cholesterol

Separate oxidation reactions are carried out using different conditions.
- cold, dilute acidified $\mathrm{KMnO}_{4}$
- hot, concentrated acidified $\mathrm{KMnO}_{4}$

Which statements about the products formed are correct?

cold, dilute acidified $\mathrm{KMnO}_{4}$ : number of hydroxy groups present

hot, concentrated acidified $\mathrm{KMnO}_{4}$ : number of 6-membered rings remaining

1

2

1

3

2

3

[Maximum number: 1]

Hex-2-ene can be made by the reaction shown.

Which statement about this reaction is correct?

A

$\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CO}^{-}$ is behaving as a Brønsted-Lowry base.

B

$\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CO}^{-}$ is behaving as an oxidising agent.

C

The C-I bond breaks via homolytic fission.

D

This is a hydrolysis reaction.

[Maximum number: 1]

Which substance reacts with trichloroethene to give a chiral product?

A

$\mathrm{Br}_{2}$

B

HCl

C

NaCN

D

NaOH

[Maximum number: 1]

Limonene is found in lemon and orange oils.

limonene

What will be the major product when limonene is reacted with an excess of dry hydrogen chloride?

A

B

C

D