Match the reactions of propene (List I) with the major organic product (List II). List I: (P) HBr, no peroxide; (Q) HBr with peroxide; (R) BH3.THF, then H2O2/NaOH; (S) Hg(OAc)2/H2O, then NaBH4. List II: (1) propan-2-ol; (2) propan-1-ol; (3) 1-bromopropane; (4) 2-bromopropane.

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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2047

Match the reactions of propene (List I) with the major organic product (List II). List I: (P) HBr, no peroxide; (Q) HBr with peroxide; (R) $BH X_{3} \cdot THF$ , then $H X_{2} O X_{2} / NaOH$ ; (S) $Hg (OAc) X_{2} / H X_{2} O$ , then $NaBH X_{4}$ . List II: (1) propan-2-ol; (2) propan-1-ol; (3) 1-bromopropane; (4) 2-bromopropane.

AP-3, Q-4, R-1, S-2
BP-4, Q-3, R-1, S-2
CP-4, Q-3, R-2, S-1
DP-3, Q-4, R-2, S-1

Answer: C

P: ionic Markovnikov addition gives 2-bromopropane (4). Q: radical addition gives 1-bromopropane (3). R: anti-Markovnikov hydration gives propan-1-ol (2). S: Markovnikov hydration gives propan-2-ol (1). So P-4, Q-3, R-2, S-1.

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Answer: C

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