JEE Main Chemistry question
An organic compound (A) with molecular formula C₉H₁₀O forms an orange-red precipitate with 2,4-DNP reagent and gives a yellow precipitate on heating with iodine and NaOH. It does not reduce Tollens' reagent or Fehling's solution, nor does it decolourize bromine water (as Baeyer's reagent). On drastic oxidation with chromic acid, it gives a carboxylic acid having molecular formula C₇H₆O₂. Identify the compound (A).
Solution
A is a carbonyl compound (positive 2,4-DNP) that is a methyl ketone (positive iodoform test) but not an aldehyde (negative Tollens'/Fehling's) and has no alkene (no bromine water decolourization). Drastic oxidation giving benzoic acid (C₇H₆O₂) means the ring is attached through a carbon chain that is oxidatively
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