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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4067

Trimethyl(1-phenylpropan-2-yl)ammonium hydroxide, , is heated. The major alkene is

  1. A1-phenylprop-1-ene,
  2. Bno alkene; only an alcohol is formed
  3. C3-phenylprop-1-ene (allylbenzene),
  4. D2-phenylprop-1-ene,

Answer: A

The Hofmann rule alone would remove a methyl hydrogen to give allylbenzene. However, the benzylic hydrogens are much more acidic, and the E2 transition state has carbanion character and gains conjugation with the ring. Loss of the benzylic hydrogen therefore dominates and the conjugated 1-phenylprop-1-ene is the major product.
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