Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

Compound B appears in several perfumes and flavourings. It is prepared by hydrogenating compound A. In the reaction, every hydrogen atom adds to the same side of the benzene ring.
(a(i))[1]

Suggest suitable reagents and conditions for this reaction.

(a(ii))[1]

Circle every chiral atom on the structure of B above.

(a(iii))[1]

How many possible optical isomers have the same structural formula as B?

(a(iv))[1]

Complete the following part-structure so that it shows the structure of one of the isomers of B that would be formed in the reaction above.

(b(i))[1]

Suggest the structure of the intermediate cation C and draw it in the box above.

(b(ii))[4]

Suggest reagents and conditions for the following steps: step 1 step 2 step 3

(c)[5]

Suggest the structures of the organic products formed when each of compounds A and B reacts with the following reagents. If no reaction occurs, write ‘no reaction’ in the relevant box. Reagents: $\text{HBr}$, $\text{Na}$, $\text{NaOH}(aq)$.

Worked solution & mark scheme

This 14-mark question has a full step-by-step worked solution and mark scheme. One marking point: Reduction using $H_2$ with Pt/Ni/Pd catalyst and heat ($50^\circ C<T<500^\circ C$)

  • Full mark scheme, point by point
  • Step-by-step worked solution
  • Write your answer & get it marked instantly by AI