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JEE Advanced levelNumerical answerDifficulty 3 of 3g3232

The alkene shown adds HBr through a carbocation. Bromide captures both the first-formed cation and the cation formed after a 1,2-hydride shift, giving two constitutionally different bromoalkanes. Count the distinct bromoalkane stereoisomers formed in total, counting enantiomers separately. Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 3

The alkene shown is 3-methylbut-1-ene. Protonation gives the secondary 3-methylbutan-2-yl cation, which is trapped as 2-bromo-3-methylbutane (one stereocentre, so 2 enantiomers). A 1,2-hydride shift gives the tertiary 2-methylbutan-2-yl cation, trapped as 2-bromo-2-methylbutane (achiral, 1 compound). Stereoisomer enumeration with RDKit confirms 2 + 1 = 3.
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