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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc034

Consider the alkenes (I) ethene, (II) propene, (III) 2-methylpropene and (IV) 3,3,3-trifluoropropene. The order of reactivity towards electrophilic addition of (fastest to slowest) is

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

Answer: A

The slow step is protonation to a carbocation, so reactivity follows cation stability. 2-Methylpropene gives a tertiary cation, propene a secondary cation, ethene a primary cation. The strongly electron-withdrawing group destabilises the developing cation and also lowers the pi electron density, making IV the slowest.
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