?-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 ?-Ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments:

(a) How many double bonds does ?-Ocimene have?

(b) Is ?-Ocimene conjugated or non-conjugated?

(c) Propose a structure for ?-Ocimene.

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

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|CHзсCHз Cнас—сн Pyruvaldehyde нссн:сH HCH Malonaldehyde Acetone Formaldehyde