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Q.a. Complete the following reaction: CH3-CH=CH2 + HBr, shown branching into two pathways — one direct pathway giving one product, and a second pathway in the presence of H2O2 giving another product. OR b. What happens when calcium carbide reacts with water? Write the reaction.

Nagaland NbseNagaland Board of School Education (Class XI) 2023Subjective· 2mImportance★★★★★
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a. HBr adds to propene by Markovnikov's rule normally, but by anti-Markovnikov's rule in presence of H2O2 (peroxide effect). b. Calcium carbide + water gives calcium hydroxide and acetylene gas.

Part (a):

Propene, CH3−CH=CH2CH_3-CH=CH_2, reacting with HBr:

  • Without peroxide (top pathway): addition follows Markovnikov's rule — H adds to the carbon already bearing more hydrogens (C1), Br adds to the more substituted carbon (C2), via the more stable secondary carbocation intermediate: CH3−CH=CH2+HBr→CH3−CHBr−CH3  (2-bromopropane)CH_3-CH=CH_2 + HBr \rightarrow CH_3-\underset{Br}{CH}-CH_3 \;(\text{2-bromopropane})
  • With H2O2 (bottom pathway, the peroxide/Kharasch effect): the mechanism switches to a free-radical chain mechanism, reversing the regiochemistry to anti-Markovnikov addition: …

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