File Preview The following is a total synthesis of the pheromone of the western pine beetle. Such syntheses are interesting both because of the organic chemistry, and because of the possibility of using species specific insecticides, rather than broad band insecticides. Provide the reagents for each step. There is some chemistry from our most recent chapter in this synthesis, but other steps are review from earlier chapters. (8 points) COOEt COOEt A C COOEt COOEt COOH B OH OTS CN D E See the last homework set F for assistance on this one. H+, H₂O G OH OH The last step is just nucleophilic addition reactions, taking the ketone to an acetal, intramolecularly. But it is hard to visualize the three dimensional shape as it occurs. Frontalin, pheromone of the western pine beetle

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter5: Resonance
Section: Chapter Questions
Problem 8E
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The following is a total synthesis of the pheromone of the western pine beetle. Such
syntheses are interesting both because of the organic chemistry, and because of the possibility of
using species specific insecticides, rather than broad band insecticides. Provide the reagents for
each step. There is some chemistry from our most recent chapter in this synthesis, but other
steps are review from earlier chapters. (8 points)
COOEt
COOEt
A
C
COOEt
COOEt
COOH
B
OH
OTS
CN
D
E
See the last homework set
F
for assistance on this one.
H+, H₂O
G
OH
OH
The last step is just nucleophilic addition reactions, taking the
ketone to an acetal, intramolecularly. But
it is hard to visualize the three dimensional shape as
it occurs.
Frontalin, pheromone of the western pine beetle
Transcribed Image Text:File Preview The following is a total synthesis of the pheromone of the western pine beetle. Such syntheses are interesting both because of the organic chemistry, and because of the possibility of using species specific insecticides, rather than broad band insecticides. Provide the reagents for each step. There is some chemistry from our most recent chapter in this synthesis, but other steps are review from earlier chapters. (8 points) COOEt COOEt A C COOEt COOEt COOH B OH OTS CN D E See the last homework set F for assistance on this one. H+, H₂O G OH OH The last step is just nucleophilic addition reactions, taking the ketone to an acetal, intramolecularly. But it is hard to visualize the three dimensional shape as it occurs. Frontalin, pheromone of the western pine beetle
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