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JEE Main 2025 · Chemistry · Hydrocarbons · medium

3-Methylbut-1-ene reacts with HBr (no peroxide). The major product is

Single correct option

33-Methylbut-1-ene reacts with HBr\mathrm{HBr} (no peroxide). The major product is
  1. A. 1-bromo-3-methylbutane
  2. B. 2-bromo-3-methylbutane
  3. C. 2-bromo-2-methylbutane
  4. D. 1-bromo-2-methylbutane
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Answer: (C) 2-bromo-2-methylbutane

Protonation of CH2=CH−CH(CH3)2\mathrm{CH_2=CH-CH(CH_3)_2} at the terminal carbon gives the secondary cation CH3−C+H−CH(CH3)2\mathrm{CH_3-\overset{+}{C}H-CH(CH_3)_2} (Markovnikov). A 1,2-hydride shift converts it into the more stable tertiary cation CH3CH2−C+(CH3)2\mathrm{CH_3CH_2-\overset{+}{C}(CH_3)_2}, which is captured by Br−\mathrm{Br^-} to give 2-bromo-2-methylbutane as the major product; 2-bromo-3-methylbutane is the minor unrearranged product.
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