Chemistry 9701 · AS & A Level · Hydrocarbons

Hydrocarbons — practice question

Benzene reacts with D, in the presence of a suitable catalyst, to form cumene and inorganic product E. This reaction is an electrophilic substitution reaction.
(a(i))[2]

Name the reactant D and the inorganic product E.

(a(ii))[1]

Give the name of the aromatic electrophilic substitution reaction taking place.

(b(i))[1]

Cumene undergoes substitution with chlorine to produce several different isomeric compounds with formula $\text{C}_9\text{H}_{11}\text{Cl}$. Substitution may happen either on the aromatic ring or on the side-chain of cumene. Describe the conditions used to make sure substitution occurs only in the aromatic ring.

(b(ii))[1]

Draw the structures of the two major isomeric products of the reaction, formula $\text{C}_9\text{H}_{11}\text{Cl}$, when substitution occurs in the aromatic ring.

(b(iii))[1]

Describe the conditions used to ensure substitution takes place only in the side-chain.

(b(iv))[1]

Draw the structures of two isomeric products of the reaction, formula $\text{C}_9\text{H}_{11}\text{Cl}$, when substitution occurs in the side-chain.

(c)[2]

Complete the following table to show the structures of the organic products formed when cumene reacts with each reagent: hot $\text{KMnO}_4(\text{aq})$ and $\text{H}_2$ with Ni at high pressure.

(d)[4]

Cumene can be nitrated using a mixture of concentrated nitric and sulfuric acids. The mechanism for this reaction is the same as the mechanism for the nitration of benzene. Complete the mechanism for this reaction. - Include all relevant charges and curly arrows to show the movement of electron pairs. - Draw the structure of the intermediate. - You do not need to draw the products.

Worked solution & mark scheme

This 13-mark question has a full step-by-step worked solution and mark scheme. One marking point: D = 2-chloropropane; E = hydrogen chloride.

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