ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
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Chapter 26.8, Problem 28CC
Interpretation Introduction

Interpretation:

A mechanism for biosynthesis of α -farnesene starting with dimethylallyl pyrophosphate and isopentenyl pyrophosphate need to be drawn.

Concept introduction:

Terpenes are constructed from dimethylallyl pyrophosphate and isopentenyl pyrophosphate.  In the synthesis of terpene pyrophosphate is the leaving group as it is a weak base. Nucleophilic attack happens to form another carbocation.  Finally proton transfer happens to give the final product.

The terpene synthesis involves the following steps,

  • Loss of OPP (pyrophosphate group)
  • Nucleophilic attack
  • Deprotonation

The above three steps are repeated again and again.  In each step and isoprene unit is added more.  Finally to obtain α -farnesene, the formed farnesyl pyrophosphate undergoes elimination.

To draw: a mechanism for the given transformation.

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