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Chapter 2: Problem 62

The conversion can be successfully carried out by (a) \(\mathrm{H}^{+} / \mathrm{H}_{2} \mathrm{O}\) (b) Hydroboration-oxidation (c) HBr addition in the presence of peroxides followed by hydrolysis with aqueous KOH (d) Oxymercuration-reduction

Short Answer

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a) H+ / H2O b) Hydroboration-oxidation c) HBr addition + Hydrolysis d) Oxymercuration-reduction Answer: All the given reactions (a), (b), (c), and (d) can successfully convert an alkene into an alcohol.

Step by step solution

01

Reaction (a): \(\mathrm{H}^{+} / \mathrm{H}_{2} \mathrm{O}\)

This reaction involves the addition of \(\mathrm{H}^{+}\) and \(\mathrm{H}_{2} \mathrm{O}\) to an alkene, following Markovnikov's rule. The alkene's double bond will break, allowing the hydrogen and a hydroxyl group (from the water molecule) to attach to the carbons of the alkene. This process results in the formation of an alcohol.
02

Reaction (b): Hydroboration-oxidation

Hydroboration-oxidation involves two main steps: 1) the addition of borane (BH3) to an alkene, and 2) the oxidation of the resulting organoborane with hydrogen peroxide (H2O2) and hydroxide ions (OH-). This reaction converts alkenes into alcohols through an anti-Markovnikov addition of H and OH groups.
03

Reaction (c): HBr addition + Hydrolysis

This reaction involves the addition of HBr to an alkene in the presence of peroxides (anti-Markovnikov). Peroxides cause a radical reaction to occur, resulting in the formation of a bromoalkane. Subsequent hydrolysis with aqueous KOH will replace the bromine atom with a hydroxyl group, resulting in the formation of an alcohol.
04

Reaction (d): Oxymercuration-reduction

Oxymercuration-reduction involves the addition of mercuric acetate (Hg(OAc)2) to an alkene in the presence of water, followed by a reduction with sodium borohydride (NaBH4). This process occurs via a Markovnikov addition and results in the formation of an alcohol, without the risk for rearrangement as in the acid-catalyzed reaction. In summary, all of the given reactions (a), (b), (c), and (d) can successfully convert an alkene into an alcohol, with either Markovnikov or anti-Markovnikov addition rules, depending on the reaction conditions.

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