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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3046

On heating in ethanol (no added base), which of the following bromides give a substitution product whose carbon skeleton or substituent position has changed through a carbocation rearrangement?

  1. A
  2. B
  3. C
  4. D

Answer: A, C, D

Option 1: methyl shift from the quaternary carbon converts the secondary into a tertiary cation. Option 3: the primary neopentyl system ionises with methyl migration to the tertiary . Option 4: the cation rearranges by methyl shift to the tertiary cation. Option 2 already gives a tertiary cation, so no shift occurs.
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