MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms II: Electrophilic and Radical Reactions / Anti-Markovnikov addition of HBr
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o2107

Which of the following alkenes give the same major product with HBr in the dark and with HBr in the presence of peroxide?

  1. Aethene
  2. Bcyclohexene
  3. C2-methylpropene
  4. Dpent-1-ene

Answer: A, B

Peroxide changes only the regiochemistry. Ethene and cyclohexene are symmetrical, so both ends of the double bond are equivalent and the bromoalkane is the same. 2-Methylpropene and pent-1-ene are unsymmetrical, so the dark reaction gives the Markovnikov bromide while the peroxide reaction gives the primary bromide.
Practice Organic Reaction Mechanisms II: Electrophilic and Radical Reactions More on Anti-Markovnikov addition of HBr

More questions on Anti-Markovnikov addition of HBr