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JEE Main levelSingle correct optionDifficulty 2 of 3o4275

The compound shown is warmed with a trace of dilute sodium hydroxide, and water is lost. Which structure is the major product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: D

The compound is 4-hydroxy-4-methylpentan-2-one, a beta-hydroxy ketone. Hydroxide removes the acidic alpha-hydrogen on C-3, and the enolate expels hydroxide from C-4 (E1cB). This gives the conjugated enone 4-methylpent-3-en-2-one (mesityl oxide), which is more stable than the non-conjugated isomer. Acetone would arise from the reverse aldol reaction.
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