Chemistry 9701 · AS & A Level · Hydroxy compounds

Hydroxy compounds — practice question

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

Write the equation for the reaction between $\text{C}_6\text{H}_5\text{OH}$ and Na.

(a(ii))[1]

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

(b)[3]

Complete the mechanism in Fig. 9.3 for the reaction of $\text{C}_6\text{H}_5\text{O}^-$ with $\text{CO}_2$. Show all required curly arrows, dipoles and charges. Draw the structure of the organic intermediate.

(c(i))[1]

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

(c(ii))[1]

Fig. 9.5 shows another Diels-Alder reaction of buta-1,3-diene. 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: Balanced equation: $\text{C}_6\text{H}_5\text{OH} + \text{Na} \rightarrow \text{C}_6\text{H}_5\text{ONa} + \tfrac{1}{2}\text{H}_2$

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