Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

Predict the products formed in the following reactions and draw their structures in the boxes provided. Remember that the molecular formula of the final product is supplied in each case.
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Predict the products of the three reaction sequences shown: chlorination with $\text{Cl}_2$ and light, then reaction with $\text{NaOH}$ and heat, to form a product with molecular formula $\text{C}_8\text{H}_{10}\text{O}$; chlorination with $\text{Cl}_2$ and $\text{AlCl}_3$, then nitration with $\text{HNO}_3$ and $\text{H}_2\text{SO}_4$ at $55^{\circ}\text{C}$, to form a product with molecular formula $\text{C}_8\text{H}_8\text{ClO}_2\text{N}$; and oxidation with $\text{KMnO}_4$ in alkaline conditions, followed by acidification and esterification with $\text{CH}_3\text{OH}$ and concentrated $\text{H}_2\text{SO}_4$ and heat, to form a product with molecular formula $\text{C}_{10}\text{H}_{10}\text{O}_4$.

Worked solution & mark scheme

This 6-mark question has a full step-by-step worked solution and mark scheme. One marking point: Aromatic substitution products drawn correctly, with orientation ignored as stated

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