Alkylation of malonic acid diethyl ester mechanism?

14Jacky04By14Jacky04

Hello there,

I'm currently doing an organic lab course at university, and we have to do pre-tests for all experiments, including reaction mechanisms. I've managed all of them so far, but I didn't fully understand the alkylation even back then. I can't come up with a sensitive reaction mechanism.

Could someone help me? Alkylation is carried out with 1-bromobutane over potassium carbonate (see picture).

Thanks in advance!

best regards

Jacky

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Picus48
Picus48
1 year ago

This is simply a nucleophilic substitution of the bromine atom in the bromobutane by the malonatanion. The alpha-C is rather acidic and cleaves a proton there by the two carboxylate functions. The remaining carbanion then attacks nucleophile on the C1 of the bromobutane and bromide flies out.

I am surprised, however, that the folded base potassium carbonate is already sufficient here. In my syntheses, I usually used metallic sodium in non-protic solvents to dissolve H from alpha-C.

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