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Ozonolysis of alpha-terpinene

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Ignore Structure A in the attached .jpg for this problem. Use only structures C and B

Alpha -Terpinene, C10H16, a terpene found in coriander oil, absorbs only two moles of hydrogen, forming p-menthane, C10H20. Ozonolysis of Alpha -terpinene yields structure C in the attached .jpg; permanganate cleavage yields structure B.

1. How many rings, if any, are in Alpha -terpinene?

2. On the basis of the cleavage products C and B and the isoprene rule, what is the most likely structure for Alpha terpinene?

3. How do you account for the presence of the OH groups in structure B?

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This solution addresses three bonding and formation questions in chemistry.

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