Chemistry 9701 · AS & A Level · Hydrocarbons

Hydrocarbons — practice question

Benzene, $\mathrm{C_6H_6}$, may be derived from crude oil.
(a(i))[1]

Benzene reacts with bromine in the presence of a suitable catalyst to form bromobenzene as one product. State the name or formula of the other product in this reaction.

(a(ii))[2]

With the catalyst present, bromine may be regarded as generating the electrophile $\mathrm{Br^+}$. Finish the mechanism for the reaction of benzene with $\mathrm{Br^+}$, using curly arrows to indicate the movement of electron pairs.

(a(iii))[1]

Name the mechanism shown.

(b(i))[2]

Benzene may serve as the starting material for the synthesis of cyclohexylmethanol, $\mathrm{C_6H_{11}CH_2OH}$, as shown. Identify a suitable reagent and a suitable catalyst for step 1.

(b(ii))[1]

Draw the displayed structure of $A$.

(b(iii))[2]

Identify appropriate reagents for steps 3 and 4.

(b(iv))[1]

Deduce the number of peaks in the $^{13}$C NMR spectrum of cyclohexylmethanol.

Worked solution & mark scheme

This 10-mark question has a full step-by-step worked solution and mark scheme. One marking point: hydrogen bromide ($HBr$)

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