Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 12, Problem 12.55P
Interpretation Introduction

Interpretation:

The product of the given reaction is to be predicted.

Concept introduction:

The hydroboration-oxidation reaction of an alkene is a syn anti-Markovnikov addition of the water molecule across the double bond.

In the first step, a proton from BH3 adds to the less substituted carbon of the double bond while the remaining fragment adds to the less substituted carbon. In the next step, alkyl borane is oxidized to alkyl borate ester by the action of basic H2O2. Finally, alkyl borate ester is hydrolyzed by the solvent (H2O) to the final product.

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Organic Chemistry: Principles and Mechanisms (Second Edition)

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