Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular

Chapter 12, Problem 12.55

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Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular formula C10H16, both yield 2,6-dimethyloctane when treated with H2 and a Pd catalyst. Ozonolysis of oximene forms (CH3)2C O, CH2 O, CH2(CHO)2, and CH3COCHO. Ozonolysis of myrcene yields (CH3)2C O, CH2 O (two equiv), and HCOCH2CH2COCHO. Identify the structures of oximene and myrcene.

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