Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

$1,3$-dimethylbenzene serves as a valuable starting material for a range of commercially significant compounds.
(a(i))[1]

The only by-product in step $2$ is $\text{HCl}$. Suggest the reagent used for this step.

(a(ii))[1]

Suggest the type of reaction taking place in both step $2$ and step $3$.

(a(iii))[1]

State the reagents and conditions needed for step $3$.

(a(iv))[2]

Suggest the structures of the two products formed when $A$ reacts with alkaline aqueous iodine.

(a)

The artificial ‘musk ketone’, $A$, is a perfume ingredient used in many cosmetics and detergents. It is prepared from 1,3-dimethylbenzene by the route shown.

(b)

1,3-dimethylbenzene is also used as a starting material in the preparation of the polymer Nomex, which is found in fireproof protective clothing worn by firefighters, military pilots and racing car drivers. The polymer is synthesised from 1,3-dimethylbenzene and 1,3-dinitrobenzene by the route shown.

(b(i))[1]

Draw the structure of one repeat unit of Nomex in the box above.

(b(ii))[1]

What kind of polymer is Nomex?

(b(iii))[1]

Suggest the by-product formed during step 3.

(b(iv))[1]

Suggest reagents and conditions for step 2.

(b(v))[1]

Suggest how and why the properties of the polymer might change if some of the diamine monomer were replaced with 1,3,5-triaminobenzene.

Worked solution & mark scheme

This 10-mark question has a full step-by-step worked solution and mark scheme. One marking point: ethanoyl chloride or $\mathrm{CH_3COCl}$

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