This is in Vollhardt & Schore\'s Organic Chemistry, 5th ed.,p.688, question 15-1

Question

This is in Vollhardt & Schore's Organic Chemistry, 5th ed.,p.688, question 15-13.

Basically, cyclooctatraene has an isomer that's a cyclohexadienefused with a butene, all double bonds on the far side of the ringfusion, two cis hydrogens at the fused location, both pointingup.

It gives a wacky bicyclic product, and I don't for the life of mesee the mechanism.

This isn't for a test, I'm just...I'm very curious, and I've mademodels, and I'm still flummoxed, and I was wondering if any of youcan see what's going on here, and show me. I promise gratitude andhigh answer ratings.

Thanks!

Explanation / Answer

I don't have that textbook anymore but if you would post the reactants, the skeletal structures, I will look at it.  I used to be pretty good at Diels Alder.

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