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Which of the following reactions will yield 1-bromo-3,3-dimethylbutane as the major product?

Options

  1. A3,3-Dimethylbut-1-ene + HBr in the presence of peroxide
  2. B3,3-Dimethylbut-1-ene + HBr in the absence of peroxide
  3. C2,3-Dimethylbut-1-ene + HBr in the presence of peroxide
  4. D3,3-Dimethylbut-1-ene + HCl in the presence of peroxide

Correct answer

A. 3,3-Dimethylbut-1-ene + HBr in the presence of peroxide

Step-by-step solution

The target product is 1-bromo-3,3-dimethylbutane, which is a primary alkyl bromide. To obtain a primary alkyl bromide from a terminal alkene without altering the carbon skeleton, anti-Markovnikov addition is required. This is achieved by the reaction of the alkene with HBr in the presence of a peroxide (Kharasch effect). The starting alkene must have the same carbon skeleton. Thus, 3,3-dimethylbut-1-ene reacting with HBr and peroxide will yield 1-bromo-3,3-dimethylbutane. In the absence of peroxide, HBr would under

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