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NEET levelSingle correct optionDifficulty 1 of 3o2003

Which reagent sequence converts $CH X_{3} - CH = CH X_{2}$ mainly into propan-1-ol?

A $BH X_{3} \cdot THF$ , then $H X_{2} O X_{2} / NaOH$
B $Hg (OAc) X_{2}$ , $H X_{2} O$ , then $NaBH X_{4}$
Cdilute $H X_{2} SO X_{4}$ in water
D $HBr$ , then aqueous $NaOH$ (no peroxide)

Answer: A

Hydroboration-oxidation places boron, and hence OH, on the less substituted carbon, giving the anti-Markovnikov alcohol propan-1-ol. Acid hydration and oxymercuration-demercuration both give propan-2-ol. HBr without peroxide gives 2-bromopropane, which would give propan-2-ol.

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