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PROBLEM 10.68

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Organic Chemistry
Found in: Page 424

Short Answer

Question: Alkene A can be isomerized to isocomene, a natural product isolated from goldenrod, by treatment with TsOH. Draw a stepwise mechanism for this conversion. (Hint: Look for a carbocation rearrangement.)

Answer

See the step by step solution

Step by Step Solution

Isomerization of alkene

The isomerization alkene occurs by the formation of a carbocation intermediate.

This intermediate carbocation leads to 1,2-bond shift (driving force is the relaxation of the strained molecule), which forms another isomer of the alkene.

Explanation

The given alkene compound is acidified by TsOH to form a tertiary carbocation intermediate. Further, the 1,2-bond shift occurs from the highly strained four-membered ring to give another alkene isomer.

Isomerization of the alkene

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