Solution
Core Logic
Compound P (C₆H₁₂O₃) gives a positive iodoform test, indicating it has a methyl ketone group (CH₃CO-). It gives a negative Tollen's test, indicating no free aldehyde group.
On acidic hydrolysis, P yields Q. Compound Q gives both positive iodoform test and Tollen's test, meaning Q contains both a methyl ketone and an aldehyde group.
Looking at the options, if P is an acetal of an aldehyde, acidic hydrolysis will regenerate the aldehyde. Option 2 is CH₃-CO-CH₂-CH(OCH₃)₂ (an acetal of aldehyde). This compound 'P' has a CH₃CO- group (positive iodoform) and an acetal (protected aldehyde, negative Tollen's). On hydrolysis:
CH₃-CO-CH₂-CH(OCH₃)₂ H₂O/H^+ CH₃-CO-CH₂-CHO + 2CH₃OHThe product Q (CH₃-CO-CH₂-CHO) has a methyl ketone (positive iodoform test) and an aldehyde (positive Tollen's test).
Pattern Recognition
Whenever an aldehyde test becomes positive after hydrolysis, it points to a protected aldehyde, usually an acetal or hemiacetal. A compound with molecular formula Cₙ H₂ₙ O₃ often represents a keto-acetal.
Chapter Mix
Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids Class 12 Chemistry: Alcohols, Phenols and Ethers