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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