A compound known as matsuone is the sex pheromone of the pine bast scale, and it was synth...

A compound known as matsuone is the sex pheromone of the pine bast scale, and it was synthesized in several steps from the alcohol citronellol. A key intermediate in the synthesis was the nitrile (S)-4,8-dimethyl-7-nonenenitrile. Show how this nitrile could be prepared from citronellol in two steps.

(The arrow ⇒ signifies that the compound shown on the left (the target) can be made from the one on the right. A step shown in this reverse way is referred to as a retrosynthetic step. The concept of retrosynthesis is developed further in Chapter 14.)