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.

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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.

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Step : III

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

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I am M.Sc (chemistry ) from punjabi university. I am a science teacher with expertise in chemistry, with 8 years of experiance in teaching. i am getting a handsome salary , now i wish to help out the people who need me UNCONDITIONALLY. and I am constantly working on creating a new and easy way of learning the tough things in an effective way. I am constantly working to make authentic and reliable information to be shared with my students and widen the horizons of knowledge.

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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