Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 9.5, Problem 20P

(a)

Interpretation Introduction

Interpretation:

Among the given compounds, the one which is more reactive in a SN1 reaction has to be identified.

Concept Introduction:

Vinyl and aryl halides: (SN1 reaction)

Vinylic halides and aryl halides do not undergo SN1 reaction because vinyl and aryl cations are even more unstable than primary carbocation.

The positive charge on a vinylic or aryl cation would be an sp carbon.  sp carbons are more resistant to become positively charged than the sp2 carbons.

(b)

Interpretation Introduction

Interpretation:

Among the given compounds, the one which is more reactive in a SN1 reaction has to be identified.

Concept Introduction:

Vinyl and aryl halides: (SN1 reaction)

Vinylic halides and aryl halides do not undergo SN1 reaction because vinyl and aryl cations are even more unstable than primary carbocation.

The positive charge on a vinylic or aryl cation would be an sp carbon.  sp carbons are more resistant to become positively charged than the sp2 carbons.

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