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 $\text{C}_{10}\text{H}_{10}\text{O}_4$.
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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