Considering which of the OH groups should be more accessible to MsCl, suggest a mechanismfor the rearrangement of the cyclobutane to the cyclopentane.MeMeMeMeEt3N, MSCIOH-30 to 4 °COHMeMe

Step 1: Step 2: Step 3: Step 4:

Answered: Considering which of the OH groups…

Organic Chemistry

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Publisher:John E. McMurry

Chapter27: Biomolecules: Lipids

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Problem 47AP: Cembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV...

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Cembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV absorption at 245 nm, but dihydrocembrene (C20H34), the product of hydrogenation with 1 equivalent of H2, has no UV absorption. On exhaustive hydrogenation, 4 equivalents of H2 react, and octahydrocembrene, C20H40, is produced. On ozonolysis of cembrene, followed by treatment of the ozonide with zinc, four carbonylcontaining products are obtained: Propose a structure for cembrene that is consistent with its formation from geranylgeranyl diphosphate.
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Considering which of the OH groups should be more accessible to MsCl, suggest a mechanism for the rearrangement of the cyclobutane to the cyclopentane. Me Me Me Me Et3N, MSCI OH -30 to 4 °C OH Me Me