b-Ocimene is a pleasant-smelling hydrocarbon found in the
Chapter 14, Problem 14(choose chapter or problem)
b-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 b-ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: Acetone CH3C O O CH3CCH3 CH O Malonaldehyde O O HCCH2CH Formaldehyde Pyruvaldehyde O HCH (a) How many double bonds does b-ocimene have? (b) Is b-ocimene conjugated or nonconjugated? (c) Propose a structure for b-ocimene. (d) Write the reactions, showing starting material and products
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