The reagent which can be used for the given transformation is to be determined. Concept introduction: The conversion of an alkene to alcohol is carried out by the oxymercuration-reduction reaction. Rearrangement generally does not take place with oxymercuration-reduction because a carbocation intermediate is not formed. The intermediate is a cyclic mercurinium ion. The product of oxymercuration-reduction follows Markovnikov’s rule. The hydroxyl group (OH) is added to the more substituted carbon atom of the initial double bond. The oxymercuration-reduction carried out with Hg ( OAc ) 2 , H 2 O/THF followed by a reduction using NaBH 4 , ethanol respectively.

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Chapter 12, Problem 12.14P

Interpretation Introduction

Interpretation:

The reagent which can be used for the given transformation is to be determined.

Concept introduction:

The conversion of an alkene to alcohol is carried out by the oxymercuration-reduction reaction. Rearrangement generally does not take place with oxymercuration-reduction because a carbocation intermediate is not formed. The intermediate is a cyclic mercurinium ion.

The product of oxymercuration-reduction follows Markovnikov’s rule. The hydroxyl group (OH) is added to the more substituted carbon atom of the initial double bond. The oxymercuration-reduction carried out with Hg(OAc)2, H2O/THF followed by a reduction using NaBH4, ethanol respectively.

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