ORGANIC CHEMISTRY-PRINT MULTI TERM
ORGANIC CHEMISTRY-PRINT MULTI TERM
4th Edition
ISBN: 9781119832614
Author: Klein
Publisher: WILEY
Question
Book Icon
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.

Blurred answer
Students have asked these similar questions
Please correct answer and don't use hand rating
None
Q1: For each molecule, assign each stereocenter as R or S. Circle the meso compounds. Label each compound as chiral or achiral. + CI Br : Н OH H wo་ཡིག་ཐrow HO 3 D ။။ဂ CI Br H, CI Br Br H₂N OMe R IN I I N S H Br ជ័យ CI CI D OH
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY