JEE Advanced 2024 Chemistry question
An organic compound P having molecular formula gives ferric chloride test and does not have intramolecular hydrogen bond. The compound P reacts with 3 equivalents of to produce oxime Q. Treatment of P with excess methyl iodide in the presence of KOH produces compound R as the major product. Reaction of R with excess iso-butylmagnesium bromide followed by treatment with gives compound S as the major product. The total number of methyl group(s) in compound S is .
Solution
with a positive ferric chloride test and no intramolecular H-bond (no adjacent OH groups) is phloroglucinol, benzene-1,3,5-triol. It exists in equilibrium with its keto tautomer, cyclohexane-1,3,5-trione, and therefore forms a trioxime **Q** with 3 equivalents of
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