Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

(a(i))[1]

State the reaction mechanism.

(a(ii))[4]

Draw the mechanism for this reaction, showing all the curly arrows needed, together with any dipoles and charges.

(b)[1]

Two isomeric aromatic compounds, V and W, each have three functional groups, two of which are shown in the table. Complete the table by giving the remaining functional groups present in V and W.

(c(i))[4]

Suggest reagents for steps 1-4.

(c(ii))[3]

Deduce the structures of R, S and T and draw their structural formulae in the boxes.

(d(i))[2]

Draw the structures of the two organic products from the reaction of V and W with $\text{LiAlH}_4$.

(d(ii))[1]

Name the type of reaction occurring between $\text{LiAlH}_4$ and V or W.

(e(i))[2]

Draw the structures of the two organic products of the hydrolysis of W.

(e(ii))[1]

The products formed from the hydrolysis of W dissolve in aqueous acid, but a precipitate, X, is produced when V is hydrolysed. Draw the structure of compound X.

(e(iii))[1]

Suggest why X is insoluble in water.

Worked solution & mark scheme

This 20-mark question has a full step-by-step worked solution and mark scheme. One marking point: Electrophilic substitution

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