Home > Community > What is the product of a Dieckmann condensation of dimethyl adipate?
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Adam Brower

What is the product of a Dieckmann condensation of dimethyl adipate?

David Curran  Follow

I've given a strong hint by changing the title of your question!

  • Methoxide as a base can abstract a proton from an acidic $\alpha$-position of an ester, that is from $\ce{-C\color\red{H}_2COOMe}$.

  • The resulting carbanion/enolate can add to the other ester group of your starting material.

  • The cyclic intermediate eventually loses methoxide to form ...

This Dieckmann condensation is the intramolecular variant of a Claisen condensation.

I suggest to do it on paper!

Dieckmann condensation of methyl adipate

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Jaleel Ali  Follow
OMe is able to leave in this instance because the reaction is under basic conditions, therefore OMe is already in solution (so it is stabilized by these conditions).More
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John Packer  Follow
The only problem here is OMe- is not a good leaving group. So why does it leave? I think it owes to great stability of C=O bond.More
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