Gossyplure, the sex pheromone of the pink bollworm, is the acetic ester of 7, 11-hexadeca- dien-1-ol. The active pheromone has the Z configuration at the C7-C8 double bond and is a mixture of E,Z isomers at the C11-C12 double bond. Shown here is the Z,E isomer. CCH3 16 (7Z,11E)-7,11-Hexadecadienyl acetate Following is a retrosynthetic analysis for (7Z,11E)-7,11-hexadecadien-1-ol, which then led to a successful synthesis of gossyplure. Me 0-Si--Bu Ме Me Si--Bu Ме Me H- 0-Si--Bu + Br Me HO Br + H H Br HO, OH Br + H H
Gossyplure, the sex pheromone of the pink bollworm, is the acetic ester of 7, 11-hexadeca- dien-1-ol. The active pheromone has the Z configuration at the C7-C8 double bond and is a mixture of E,Z isomers at the C11-C12 double bond. Shown here is the Z,E isomer. CCH3 16 (7Z,11E)-7,11-Hexadecadienyl acetate Following is a retrosynthetic analysis for (7Z,11E)-7,11-hexadecadien-1-ol, which then led to a successful synthesis of gossyplure. Me 0-Si--Bu Ме Me Si--Bu Ме Me H- 0-Si--Bu + Br Me HO Br + H H Br HO, OH Br + H H
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
Related questions
Question
How might you modify this synthesis to prepare the 7 Z ,11 Z isomer of gossyplure
Transcribed Image Text:Gossyplure, the sex pheromone of the pink bollworm, is the acetic ester of 7, 11-hexadeca-
dien-1-ol. The active pheromone has the Z configuration at the C7-C8 double bond and
is a mixture of E,Z isomers at the C11-C12 double bond. Shown here is the Z,E isomer.
CCH3
16
(7Z,11E)-7,11-Hexadecadienyl acetate
Transcribed Image Text:Following is a retrosynthetic analysis for (7Z,11E)-7,11-hexadecadien-1-ol, which
then led to a successful synthesis of gossyplure.
Me
0-Si--Bu
Ме
Me
Si--Bu
Ме
Me
H-
0-Si--Bu
+ Br
Me
HO
Br + H H
Br
HO,
OH
Br + H H
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 4 steps with 6 images
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY