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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4014

3-Bromo-3-methylpentane is heated in ethanol (E1 only). The alkene formed in the greatest amount is

  1. A(E)-3-methylpent-2-ene
  2. B3-methylpent-1-ene
  3. C2-ethylbut-1-ene
  4. D(Z)-3-methylpent-2-ene

Answer: A

The tertiary cation is formed; no shift can improve it. Loss of H from a CH2 gives the trisubstituted 3-methylpent-2-ene; loss from the methyl gives disubstituted 2-ethylbut-1-ene (minor). Between E and Z isomers of 3-methylpent-2-ene the E isomer is more stable, since the two larger groups avoid each other.
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