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Developed The Claisen Condensation in 1887

Arthur Michael developed the Claisen condensation reaction in 1887. In this reaction, two molecules of an ester react in the presence of an alkoxide base to form a β-keto ester. The reaction requires that at least one reagent be enolizable and the base not interfere with the reaction. Common esters like methyl and ethyl esters are used because their alkoxy groups are good leaving groups. The base deprotonates one ester to form an enolate ion which then attacks the carbonyl carbon of a second ester molecule, joining the two and eliminating the leaving group to form the β-keto ester product.

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50 views

Developed The Claisen Condensation in 1887

Arthur Michael developed the Claisen condensation reaction in 1887. In this reaction, two molecules of an ester react in the presence of an alkoxide base to form a β-keto ester. The reaction requires that at least one reagent be enolizable and the base not interfere with the reaction. Common esters like methyl and ethyl esters are used because their alkoxy groups are good leaving groups. The base deprotonates one ester to form an enolate ion which then attacks the carbonyl carbon of a second ester molecule, joining the two and eliminating the leaving group to form the β-keto ester product.

Uploaded by

Prince Samaraj
Copyright
© Attribution Non-Commercial (BY-NC)
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
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   (1851-1930)
developed the ³Claisen Condensation´ in
1887
ï t least one of the reagents must be
enolizable (have an Į-hydrogen and be able to
undergo deprotonation to form the enolate
anion).
ï The base used must not interfere
with the reaction by undergoing nucleophilic
substitution or addition with a carbonyl carbon.
ï The alkoxy portion of the ester must
be a good leaving group. Methyl and ethyl
esters, which yield the methoxy and ethoxy
leaving groups, respectively, are usually used.
'n the Claisen reaction, two molecules of
an ester react with each other in the
presence of an alkoxide base to form a ȕ-
keto ester. 't is an intermolecular reaction.
O
    || -



mt -O - C - CH ± CH3

 
 
m  
 

O  
 
||
  
 



mt -O - C - CH2 ± CH3 
 




Útep1:The base removes a proton from the
Į-carbon to form a resonance-stabilized
enolate.
Útep2:The nucleophilic enolate attacks the
electrophilic carbonyl carbon of another
molecule of ester, forming a new C-C
bond. This join the Į-carbon of one ester
to the carbonyl carbon of a second ester.
Útep3:mlimination of the leaving group,
ethoxide ion, forms a ȕ-keto ester.
ë m
 
  


Į hydrogens
6eprotonation of mthyl Propanoate
TheResonance
enolate ion is a strong nucleophile
and will attack the partially positive
carbon of a carbonyl group.
mthyl Benzoate

mnolate of
mthyl Propanoate
Úelf condensation of ethyl propanoate

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