An organic compound X ( C ₉ H ₁₀ O ) gives a red-orange precipitate with 2,4 -DNP reagent and a yellow precipitate upon heating with iodine and aqueous NaOH . Drastic oxidation of X with alkaline KMnO ₄ followed by acidification yields a dicarboxylic acid Y. Upon heating, compound Y readily loses a molecule of water to produce an anhydride Z. The compound X is:

Step-by-step solution

Compound X ( C ₉ H ₁₀ O ) forms a red-orange precipitate with 2,4 -DNP, indicating the presence of a carbonyl group. It gives a yellow precipitate with I ₂/ NaOH (iodoform test), confirming the presence of a methyl ketone ( - COCH ₃ ) group. Drastic oxidation of X yields a dicarboxylic acid Y, meaning there are two oxidizable side chains on the benzene ring. Since X has 9 carbon atoms and contains a - COCH ₃ group ( 2 carbons), the remaining 7 carbons must form a methylphenyl group. Thus, X is a methylacetophenone