Which of the following sets of reagents will convert...

Which of the following sets of reagents will convert 1-bromo-2-phenylethane to 1 -phenylethanol? (a) $\mathrm{H}_{2} \mathrm{SO}_{4}$ and heat (b) $1 . \mathrm{NaOCH}_{2} \mathrm{CH}_{3} / \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}, 2 . \mathrm{BH}_{3} / \mathrm{dig}-$ lyme, $3 . \mathrm{H}_{2} \mathrm{O}_{2}, \mathrm{OH}^{-}$ (c) $1 . \mathrm{NaOC}\left(\mathrm{CH}_{3}\right)_{3} /\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}, 2 \cdot \mathrm{Hg}(\mathrm{OAc})_{2}$ $/ \mathrm{THF}-\mathrm{H}_{2} \mathrm{O}, 3 . \mathrm{NaBH}_{4}, \mathrm{OH}^{-}$ (d) $\mathrm{NaNH}_{2} / \mathrm{NH}_{3}$ 2. Br $/$ light, $3 . \mathrm{H}^{+} / \mathrm{H}_{2} \mathrm{O}$

Which of the following sets of reagents will convert 1-bromo-2-phenylethane to 1 -phenylethanol?
(a) $\mathrm{H}_{2} \mathrm{SO}_{4}$ and heat
(b) $1 . \mathrm{NaOCH}_{2} \mathrm{CH}_{3} / \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}, 2 . \mathrm{BH}_{3} / \mathrm{dig}-$
lyme, $3 . \mathrm{H}_{2} \mathrm{O}_{2}, \mathrm{OH}^{-}$
(c) $1 . \mathrm{NaOC}\left(\mathrm{CH}_{3}\right)_{3} /\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}, 2 \cdot \mathrm{Hg}(\mathrm{OAc})_{2}$
$/ \mathrm{THF}-\mathrm{H}_{2} \mathrm{O}, 3 . \mathrm{NaBH}_{4}, \mathrm{OH}^{-}$
(d) $\mathrm{NaNH}_{2} / \mathrm{NH}_{3}$ 2. Br $/$ light, $3 . \mathrm{H}^{+} / \mathrm{H}_{2} \mathrm{O}$

Key Concepts

Regioselectivity in Addition Reactions

Regioselectivity in addition reactions refers to the preference for an electrophile or nucleophile to add to one carbon of a double (or triple) bond over another. Understanding Markovnikov and anti-Markovnikov rules is crucial to controlling where new functional groups are introduced during synthesis.

Hydroboration–Oxidation

Hydroboration–oxidation is a two?step reaction that converts alkenes (or alkynes) to alcohols. The first step adds boron across the unsaturated bond with high regioselectivity (typically anti-Markovnikov), and the second step oxidizes the organoborane intermediate to yield the corresponding alcohol.

Oxymercuration–Demercuration

Oxymercuration–demercuration is a method for converting alkenes into alcohols without the rearrangement problems typical of acid-catalyzed hydration. The process involves the formation of a mercurial intermediate, which is subsequently reduced to form the desired alcohol, preserving the regiochemistry of the addition.

Elimination Reactions

Elimination reactions involve the removal of a leaving group along with a hydrogen atom to form a multiple bond (such as a double or triple bond). These reactions are crucial when transforming saturated compounds into unsaturated intermediates that can undergo further functionalization, such as hydroboration or halogenation.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions occur when a nucleophile replaces a leaving group in a molecule. They are fundamental in organic synthesis for transforming functional groups, and the mechanism (SN1 or SN2) depends on factors like substrate structure and reaction conditions.

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