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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1147

Compound X, , gives a crystalline bisulphite adduct, does not reduce Tollens' reagent, and gives a yellow precipitate with and . X is treated with (i) , dry ether; (ii) . The product is

  1. A3-methylbutan-2-ol
  2. B2-methylbutan-1-ol
  3. C2-methylbutan-2-ol
  4. Dpentan-2-ol

Answer: C

Bisulphite adduct plus a negative Tollens test gives a ketone, and a positive iodoform test gives a methyl ketone, so X is butan-2-one . Adding to the carbonyl and hydrolysing gives , 2-methylbutan-2-ol.
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