Stobbe reaction and its Mechanism

It is a type of condensation reaction that involves the condensation of an aldehyde or ketone with succinic ester in the presence of sodium ethoxide or Potassium ethoxide to yield unsaturated ester acid .

The complete reaction is as below.

Stobbe Reaction

The mechanism involves 3 steps , and firstly the succinate is treated with base to give the following resonance stabilized hybrid. A carboanion is formed firstly.

Step : I

Step 1 involves the condensation of carbanion and ketone.

Step : II

Step 2 shows a rearrangement and intramolecular cyclization to give a lactone-ester.


Step : III

The ring opening takes place to give the unsaturated ester acid.

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2 thoughts on “Stobbe reaction and its Mechanism

  1. thank you for providing a step by step mechanism. I found it very useful. Looking at step 3 of the mechanism, The lactone ester was not properly drawn, there is an extra hydrogen. I also think there is a need to include a fourth step acid workup/quench. Once again thank you.


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