Methyl esters (RCO2CH3) undergo a cleavage reaction to yield carboxylate ions plus iodomethane on heating with LiI
Question:
Methyl esters (RCO2CH3) undergo a cleavage reaction to yield carboxylate ions plus iodomethane on heating with LiI in dimethyl form amide: The following evidence has been obtained: (1) the reaction occurs much faster in DMF than in ethanol. (2) The corresponding ethyl ester (RCO2CH2CH3) cleaves approximately 10 times more slowly than the methyl ester. Propose a mechanism for the reaction. What other kinds of experimental evidence could you gather to support yourhypothesis?
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The two pieces of evidence indicate that the reaction procee...View the full answer
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