The sex pheromone (matsuone) of a parasitic insect (Matsucoccus) that infests pine trees w...

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.

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(b) Convert your retrosynthesis to a synthesis, showing appropriate reagents for each step.