Organic Chemistry: Principles And Mechanisms
Organic Chemistry: Principles And Mechanisms
2nd Edition
ISBN: 9780393630756
Author: KARTY, Joel
Publisher: W.w. Norton & Company,
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Chapter 12, Problem 12.46P
Interpretation Introduction

Interpretation:

It is to be explained why the given reaction violates Markovnikov’s rule.

Concept introduction:

The oxymercuration-reduction is the reaction of addition of water across the C=C bond. The alkene is first reacted with mercury (II) acetate, Hg(OAc)2, in a water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, NaBH4. The reaction proceeds through formation of a Mercurinium ion intermediate. The electron-withdrawing group at the Mercurinium ion intermediate destabilizes the ion, resulting in the product, following anti-Markovnikov rule.

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Organic Chemistry: Principles And Mechanisms

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