Caryophyllene (C₁₅H₂₄) is an unusual sesquiterpene familiar to you as a major cause of the odor of cloves. Determine its structure from the following information. (Caution: The structure is totally different from that of a-caryophyllene alcohol in Problem 72.)

Reaction 1

Reaction 2

Reaction 3

An isomer, isocaryophyllene, gives the same products as caryophyllene upon hydrogenation and ozonolysis. Hydroboration – oxidation of isocaryophyllene gives a C₁₅H₂₆O product isomeric to the one shown in reaction 3; however, ozonolysis converts this compound into the same final product shown. In what way do caryophyllene and its isomer differ?

In problem 72

Transcribed Image Text:

H, Pd-C Caryophyllene C15H28