Problem 3

Compound A, C₄H₈O₂, gives an orange precipitate with 2,4-dinitrophenylhydrazine reagent, and a silver mirror with ammoniacal silver nitrate. A is converted to B, C₄H₆O, on treatment with acid. B may exist as a cis- or trans- isomer; it reacts with hydrogen chloride to give C, C₄H₇OCl, and with chlorine to give D, C₄H₆OC1₂.

Reduction of C gives E, C₄H₉OCl, which is hydrolysed by dilute alkali to F, C₄H₁₀O₂. Both A and F give a positive iodoform (CHI₃) test, whereas E does not.

Identify compounds A to F.

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