Chemistry 9701 · AS & A Level · Hydrocarbons

Hydrocarbons — practice question

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

With a suitable catalyst present, benzene reacts with bromine to form bromobenzene as one product. Give the name or formula of the second product in this reaction.

(a(ii))[2]

In the presence of the catalyst, bromine may be treated as forming the electrophile $\mathrm{Br^+}$. Complete the mechanism showing how benzene reacts with $\mathrm{Br^+}$, using curly arrows to indicate the movement of electron pairs.

(a(iii))[1]

Name this mechanism.

(b(i))[2]

Benzene can act as the starting material in 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 structure of $A$.

(b(iii))[2]

Identify suitable reagents for steps 3 and 4.

(b(iv))[1]

Deduce the number of peaks in the carbon-13 NMR spectrum of cyclohexylmethanol.

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