ОН CN (S)-(-)-Citronellol (S)-4,8-Dimethyl-7-nonenenitrile

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry
Section4.2: Cis–trans Isomerism In Cycloalkanes
Problem 5P: Draw the structures of the following molecules: (a) trans-l-Bromo-3-methylcyclohexane (b) cis-1,...
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The sex pheromone (matsuone) of a parasitic insect (Matsucoccus) that infests pine trees was prepared in a multistep synthesis from (−)-citronellol by way of the nitrile shown.

(a) Relate the nitrile to (−)-citronellol by a retrosynthetic analysis.
(b) Convert your retrosynthesis to a synthesis, showing appropriate reagents for each step.

ОН
CN
(S)-(-)-Citronellol
(S)-4,8-Dimethyl-7-nonenenitrile
Transcribed Image Text:ОН CN (S)-(-)-Citronellol (S)-4,8-Dimethyl-7-nonenenitrile
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