(1) A compound with MF C2H2BrCl exhibits two doublets (J = 16 Hz) in its PMR spectrum. Suggest a suitable structure along with other possible structures.

(2) How can the structures of A and B be decided based on their UV spectral data?

[lambda max = 296 nm (epsilon max = 10700) and lambda max = 281 nm (epsilon max = 20800)]

[Structures A and B shown]

3Medium15 marks

The compound A, acetal of acetaldehyde, on reaction with B, under given reaction conditions, yields C and the final product D :

[Reaction scheme shown with A + B -> Propionic acid -> C -> Delta -> D]

(i) Write down the structures of the products C and D. Propose a mechanism with suitable explanation.

(ii) Write down the product(s) if ortho-ester E is used instead of the compound A under the similar reaction conditions :

[Structure E given]

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