Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

Two molecules of compound F combine under suitable conditions to produce compound G. The data provided for F and G include mass spectral evidence, $^{1}\text{H}$ NMR evidence, and the products obtained when G is heated with dilute sulfuric acid.
(a(i))[1]

Explain how the mass spectrum of F shows that one molecule of F contains seven carbon atoms. Show your working.

(a(ii))[1]

Suggest the molecular formula of the fragment of G at $m/e = 91$.

(a(iii))[2]

Suggest the molecular formulae of F and G.

(a(iv))[2]

Suggest structures for compounds F and G.

(a(v))[1]

On the structures you have drawn in part (iv), circle the protons that give the $^{1}\text{H}$ NMR peaks at $\delta = 10.0$ in F and $\delta = 5.1$ in G.

(a(vi))[1]

State the type of reaction that G undergoes when heated with dilute sulfuric acid.

(b)[3]

Describe and explain the relative acidities of benzoic acid, phenylmethanol and 4-methylphenol.

(c)[3]

Suggest a two-step route for the synthesis of 4-methylphenyl benzoate from 4-methylphenol and benzoic acid. Include reagents and conditions for each step, and the structure of the intermediate compound.

Worked solution & mark scheme

This 14-mark question has a full step-by-step worked solution and mark scheme. One marking point: Calculation shows 7 carbon atoms

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