Chapter 14.SE, Problem 50AP

β-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of β-ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments:

(a) How many double bonds does β -ocimene have?

(b) Is β -ocimene conjugated or nonconjugated?

(c) Propose a structure for β -ocimene.

(d) Write the reactions, showing starting material and products.