Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

Separate samples of phenol, $\text{C}_6\text{H}_5\text{OH}$, are treated individually with sodium and with dilute nitric acid.
(a(i))[1]

Give the equation for the reaction of $\text{C}_6\text{H}_5\text{OH}$ with Na.

(a(ii))[1]

Draw the structures of the two principal isomeric organic products that form when phenol reacts with dilute $\text{HNO}_3$.

(b)[3]

Complete the mechanism for the reaction between $\text{C}_6\text{H}_5\text{O}^-$ and $\text{CO}_2$, including the structure of the organic intermediate.

(c(i))[1]

Draw three curly arrows in Fig. 9.4 to finish the mechanism for the Diels-Alder reaction between buta-1,3-diene and ethene.

(c(ii))[1]

A second Diels-Alder reaction of buta-1,3-diene is shown in Fig. 9.5. Predict the product formed in this reaction.

Worked solution & mark scheme

This 7-mark question has a full step-by-step worked solution and mark scheme. One marking point: $\text{C}_6\text{H}_5\text{OH} + \text{Na} \rightarrow \text{C}_6\text{H}_5\text{ONa} + \tfrac{1}{2}\text{H}_2$

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