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 12.28P
Interpretation Introduction

(a)

Interpretation:

How the given compound can be synthesized from an acyclic compound is to be shown.

Concept introduction:

Compounds containing a cyclopropyl ring can be synthesized from alkenes and alkynes. When an alkene or an alkyne is treated with a carbene R2C:, the π bond is replaced by a C(R2) bridge. This results in the introduction of a cyclopropyl ring on the substrate. The ‘R’ group(s) in the carbene may be hydrogen, a halogen or a combination of these.

A carbene is a highly reactive species and is generated in situ. Common methods are irradiating diazomethane with ultraviolet light, of treating a haloform (trihalomethane) with a strong base. The carbene adds to the double bond in a concerted reaction – the lone pair on the carbene forms a bond with one carbon of the double (or triple) bond and the π bond pair simultaneously forms a bond to the carbene carbon.

Interpretation Introduction

(b)

Interpretation:

How the given compound can be synthesized from an acyclic compound is to be shown.

Concept introduction:

Compounds containing a cyclopropyl ring can be synthesized from alkenes and alkynes. When an alkene or an alkyne is treated with a carbene R2C:, the π bond is replaced by a C(R2) bridge. This results in the introduction of a cyclopropyl ring on the substrate. The ‘R’ group(s) in the carbene may be hydrogen, a halogen or a combination of these.

A carbene is a highly reactive species and is generated in situ. Common methods are irradiating diazomethane with ultraviolet light, of treating a haloform (trihalomethane) with a strong base. The carbene adds to the double bond in a concerted reaction – the lone pair on the carbene forms a bond with one carbon of the double (or triple) bond and the π bond pair simultaneously forms a bond to the carbene carbon.

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Organic Chemistry: Principles and Mechanisms (Second Edition)

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