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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o4145

4-Hydroxy-4-methylpentan-2-one is dehydrated with dilute . Which statements are correct?

  1. AThe main alkene formed is 4-methylpent-3-en-2-one (mesityl oxide).
  2. B4-Methylpent-4-en-2-one is the main product.
  3. CThe intermediate is the enolate formed by loss of H from C-3.
  4. D is lost from C-4 as the electrons of the enolate move to form the bond.

Answer: A, C, D

Removal of H from C-3 gives an enolate, which pushes out from C-4 and forms the bond conjugated with , giving mesityl oxide. The non-conjugated isomer 4-methylpent-4-en-2-one would need removal of a non-acidic methyl hydrogen on C-4 and is not the main product.
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