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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
BuyFind

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

Solutions

Chapter
Section
Chapter 27.SE, Problem 50AP
Textbook Problem

Propose a mechanism for the biosynthesis of the sesquiterpenoid trichodiene from farnesyl diphosphate. The process involves cyclization to give an intermediate secondary carbocation, followed by several carbocation rearrangements.

Chapter 27.SE, Problem 50AP, Propose a mechanism for the biosynthesis of the sesquiterpenoid trichodiene from farnesyl

Expert Solution
Interpretation Introduction

Interpretation:

A mechanism for the biosynthesis of trichodiene, a triterpenoid from farnesyl diphosphate is to be proposed.

Concept introduction:

The steps involved in the biosynthesis of trichodiene from farnesyl diphosphate are i) Loss of diphosphate ion and its reattack on the allyl carbocation ii) Elimination of the diphosphate ion by the attack of a double bond to form a carbocation with a six member ring. iii) Attack by another double bond to produce a five member ring iv) Migration of hydrogen v) Migration of two methyl groups vi) Deprotonation.

To propose:

A mechanism for the biosynthesis of trichodiene, a triterpenoid from farnesyl diphosphate.

Explanation of Solution

The loss of the diphosphate ion results in the formation of a primary carbocation which rearranges to a tertiary carbocation. In the next step the diphosphate ion gets reattached to the tertiary carbocation. The attack of one of the double bonds leads to cyclization ...

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Chapter 27 Solutions

Organic Chemistry
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