6) Frontalin (2) is an insect pheromone responsible for aggregation of Southern

Question

6) Frontalin (2) is an insect pheromone responsible for aggregation of Southern Pine Beetles, one of the most destructive insects in pines forest of the southeastern United States. The aggregation mechanism of these insects isn't perfectly known but it seems that compounds (terpenes like apinene) produced by the trees attract some female insects. The females secrete (-)-frontalin, among other pheromones, that attract a lot of male (and female) insects. A) (7 pts) Using curved arrow notation, provide a plausible mechanism for the conversion of 1 into frontaline under the conditions indicated. Be careful to show all steps (including proton transfers), and use equilibrium arrows between distinct mechanistic steps. You may use H-A and B: as generic acid/base reagents for proton transfers.

B) (1 pt) How does one drive the equilibrium in the desired direction (i.e. toward 2)?

C) (2 pts) What is the required stoichiometry (based upon 1) of TsOH?

Explanation / Answer

B. If we remove water by using Dean strork aparatus then we can get the desired product.

C. In this reaction TsOH is used catalytic amount.

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