Problem 1

Compound W, C₃H₈O, reacts with hot concentrated phosphoric acid to give X, C₃H₆, which rapidly decolourises a solution of bromine in tetrachloromethane. On treatment with ethanoyl chloride, W gives Y, C₅H₁₀O₂. Oxidation of W with potassium dichromate in dilute sulphuric acid gives Z, C₃H₆O, which gives an orange precipitate with 2,4-dinitrophenylhydrazine but does not react with an ammoniacal solution of silver nitrate.

Deduce the structures of W, X, Y and Z, explaining carefully what each piece of evidence tells you.

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