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JEE Main levelOne or more correct optionsDifficulty 2 of 3ap229

For the pinacol rearrangement of the diol shown (dilute , warm), choose all correct statements.

  1. AThe product has a tert-butyl group attached to a carbonyl carbon.
  2. BThe first carbocation is tertiary and is formed by loss of water from a protonated hydroxyl group.
  3. CThe product gives a yellow precipitate with iodine and sodium hydroxide.
  4. DThe product is an aldehyde that reduces Tollens reagent.

Answer: A, B, C

The diol is pinacol; the product is pinacolone, . It is formed through a tertiary cation followed by a methyl shift, so statements A and B hold. Pinacolone is a methyl ketone, so it gives iodoform with (C). It is a ketone, not an aldehyde, so D is wrong.
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