Malonic Ester Synthesis
The big item today was the misnomer of the title. The Malonic Ester Synthesis does NOT synthesize a malonic ester but rather starts with one and converts an alkyl halide into a carboxylic acid with a two carbon chain extension. Most of class was spent working through the mechanism, which involves deprotonation of the malonic ester (NOTE: use the correct alkoxide as base!), the SN2 reaction to add the alkyl group of the alkyl halide, a double hydrolysis and finally a decarboxylation.You should be able to work your way through the mechanism; take time to learn the decarboxylation.
Problem Set 9 and the key have been posted to the right; they will give you practice on the Malonic Ester Synthesis and also the Acetoacetic Ester Synthesis, which is our major topic for Wednesday.
Have a great pause!
posted by DCChem @ 4:44 PM
1 Comments:
If you would like to see the mechanism of acetoacetic ester synthesis I would recommend to read my article on Acetoacetic Ester Synthesis | PharmaXChange.info
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