Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
2nd Edition
ISBN: 9780393655551
Author: KARTY, Joel
Publisher: W. W. Norton & Company
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Chapter 11, Problem 11.21P
Interpretation Introduction

Interpretation:

The mechanisms for the transformation of neryl pyrophosphate to α-terpeniol and terpin hydrate are to be drawn.

Concept introduction:

Neryl pyrophosphate contains two isoprene units linked head to tail. It undergoes heterolysis to produce a resonance stabilized primary carbocation. The presence of a double bond five bonds away from the primary carbocation leads to cyclization. The double bond is a relatively electron-rich region and acts as a nucleophile. The π-bond pair moves toward the carbocation to form a stable six-membered ring.

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Chapter 11 Solutions

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)

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