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 11, Problem 11.38P
Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the given reaction with major product is to be drawn.

Concept introduction:

Alkynes are electron rich system like alkenes and can undergo electrophilic addition of water in acidic condition to produce the enol form. This enol form, on acid catalyzed tautomerization, converts to a stable keto form, i.e., corresponding aldehyde or ketone. The acid in aqueous solution gets dissociated and forms hydronium ion H3O+. The reaction proceeds with proton transfer reaction to form a stable vinylic carbocation, followed by the action of water as a nucleophile. The deuterium is a isotope of hydrogen atom and reacts like hydrogen.

Interpretation Introduction

(b)

Interpretation:

The detailed mechanism for the given reaction with major product is to be drawn.

Concept introduction:

Alkynes are electron rich system like alkenes and can undergo electrophilic addition of water in acidic condition to produce the enol form. This enol form, on acid catalyzed tautomerization, converts to a stable keto form, i.e., corresponding aldehyde or ketone. The acid in aqueous solution gets dissociated and forms hydronium ion H3O+. The reaction proceeds with proton transfer reaction to form a stable vinylic carbocation, followed by the action of water as a nucleophile. The deuterium is a isotope of hydrogen atom and reacts like hydrogen.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for the given reaction with major product is to be drawn.

Concept introduction:

Alkynes are electron rich system like alkenes and can undergo electrophilic addition of water in acidic condition to produce the enol form. This enol form, on acid catalyzed tautomerization, converts to a stable keto form, i.e., corresponding aldehyde or ketone. The acid in aqueous solution gets dissociated and forms hydronium ion H3O+. The reaction proceeds with proton transfer reaction to form a stable vinylic carbocation, followed by the action of water as a nucleophile. The deuterium is an isotope of hydrogen atom and reacts like hydrogen.

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Organic Chemistry: Principles and Mechanisms (Second Edition)

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