Return to Contents Chapter 19: Carboxylic Acids Ch 19 contents
Decarboxylation
decarboxylation removes CO2
Reaction type: Elimination

Summary

malonic acid
DECARBOXYLATION
Step 1:
Remember curly arrows flow.... Start at the protonation of the carbonyl, break the O-H bond and form the p bond, break the C-C and make the C=C. Note the concerted nature of this reaction and the cyclic transition state.
decarboxylation of malonic acid
Step 2:
Tautomerisation of the enol of the carboxylic acid leads to the acid product (not shown here).

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© Dr. Ian Hunt, Department of Chemistry, University of Calgary