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Dieckmann Condensation Reaction. Prepared by: Maram A. A. Amleh. Table of Contents. Cover Slide. Table of Content. Objectives. Background. Reaction and Mechanism. Applications. 8. Conclusion. 9. References. Objectives:. I prepared this reaction to

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Dieckmann condensation reaction l.jpg

Dieckmann Condensation Reaction

Prepared by:

Maram A. A. Amleh


Table of contents l.jpg
Table of Contents

  • Cover Slide.

  • Table of Content.

  • Objectives.

  • Background.

  • Reaction and Mechanism.

  • Applications.

    8. Conclusion.

    9. References.


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Objectives:

I prepared this reaction to

1.Learn more about dieckmann condensation reaction

2.Under stand how reaction is occour


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Background

  • The Dieckmann Condensation is an intramolecular variant of the Claisen Condensation. The reaction is most commonly used to prepare 5 or 6 membered ring ß-keto esters.

  • The formation of 5 membered rings tends to be faster than 6 membered rings, although the 6 membered ring products are generally more thermodynamically stable.

  • Ring formation becomes progressively more difficult to accomplish as the ring size of the desired product increases.



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Application :

  • The acidic hydrogen between the two carbonyl groups is deprotonated in step four. Protonation with a Brønsted-Lowry acid (H3O+ for example) re-forms the β-keto ester. This deprotonation step is the driving force for this reaction.

  • Owing to the steric stability of five- and six-membered ring structures, these will preferentially be formed. 1,4- and 1,6 diesters will form five-membered cyclic β-keto esters, while 1,5- and 1,7 diesters will form six-membered β-keto esters.


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  • The Dieckmann Condensation generally cannot be used to prepare small, highly strained ring systems. Rather than form a three membered ring, diethyl succinate undergoes an intermolecular Claisen Condensation followed by a Dieckmann Condensation to afford the six membered ring compound instead of reacting to form the three membered ring ß-keto ester as shown following.


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Conclusion alcohol that corresponds to the alcoholic moiety of the ester functional groups. The

  • The base-catalyzed intramolecular condensation of a diester. The Dieckmann Condensation works well to produce 5- or 6-membered cyclic ß-keto esters, and is usually effected with sodium alkoxide in alcoholic solvent


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References alcohol that corresponds to the alcoholic moiety of the ester functional groups. The :

  • http://www.wikipidida.com.

  • http://blog.para-gen.com.

  • www.organic-

  • chemistry.org/namedreacti...‏


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