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

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter17: Aldehydes And Ketones
Section: Chapter Questions
Problem 17.60P: 17-60 1-Propanol can be prepared by the reduction of an aldehyde, but it cannot be prepared by the...
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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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