Alpha-phellandrene, C10H16, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular formula C10H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C10H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds: CHIL-CH HOCHSCHICH CH(CH3)2 Propose a structure for alpha-phellandrene.

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy
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Problem 50AP: -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the...
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Alpha-phellandrene, C₁0H16, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular
formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula
C10H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds:
CHIC-CH HOCHSCHICH
CH(CH3)2
Propose a structure for alpha-phellandrene.
Transcribed Image Text:Alpha-phellandrene, C₁0H16, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C10H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds: CHIC-CH HOCHSCHICH CH(CH3)2 Propose a structure for alpha-phellandrene.
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Phellandrene is a cyclic monoterpene, widely spread in nature. Phellandrene was isolated from Eucalyptus phellandra and hence is named after it. It is used in fragrances.

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