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 12.25P
Interpretation Introduction

Interpretation:

The structures of the initial alkyne A and intermediate B in the reaction of A with disiamylborane, followed by a basic solution of H2O2 to produce the given aldehyde are to be drawn.

Concept introduction:

Disiamylborane ((C5H11)2BH) reacts specifically with terminal alkynes to produce an Anti-Markovnikov addition product. Only one molecule of disiamylborane adds to the alkyne because of the bulky alkyl groups attached to the boron atom. Oxidation of this addition product under the basic condition leads to the formation of an enol, which tautomerizes to an aldehyde under the reaction conditions.

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Follow the curved arrows and draw the hydrocarbon product of the following reaction. Include all lone pairs and charges as appropriate. Ignore inorganic byproducts.
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Chapter 12 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

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