A ketone A which undergoes haloform reaction gives compound B on reduction.

Question

(i) A ketone A which undergoes haloform reaction gives compound B on reduction. B on heating with sulphuric acid gives compound C, which forms mono-ozonide D. The compound D on hydrolysis in presence of zinc dust gives only acetaldehyde. Write the structures and IUPAC names of A, B and C. Write down the reactions involved.

(ii) Predict the products formed when cyclohexanecarbaldehyde reacts with following reagents.

(a) PhMgBr and then H₃O⁺.

(b) Tollens’ reagent.

Answer 1

CH₃CH=CHCH₃ 

The compound C is obtained by dehydration of B, thus the latter should be

Finally, B is obtained by the reduction of A. Hence, the compound A should be

(ii) (a)

(b)