Esterification

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Esterification is a chemical reaction of an acid with an alcohol (R'OH) to form an ester (RCOOR').

Usually esterification refers to reaction between an organic (carboxylic) acid (RCOOH) with an alcohol (R'OH) to form an ester (RCOOR') and water and called Fischer esterification. The chemical reaction for Fischer esterification is given below:

The reaction starts when the carboxylic acid accepts a proton from the strong acid catalyst.

In the second step the alcohol attacks the protonated carbonyl group to create a tetrahedral intermediate structure. In the third step a proton is lost at one oxygen atom and bonds to another oxygen atom. In the fourth step a water molecule leaves the structure. In the fifth step a proton (H+) leaves the carbonyl group, transfers to a base and ester is formed.


An animated example of this reaction is shown. Please click on the buttons below to animate the reaction with different representations. Use the popup button to enlarge the view and the quality button to turn on anti-aliasing.

The animation was originally done by Prof. Dr. Verena Pietzner; for details, see her web site ChiLe[1]. The implementation into Proteopedia was done by Prof. Jaime Prilusky, Prof. Joel L. Sussman

and Veronika Pelekhov.



Esterification of fatty acid with ethanol

Drag the structure with the mouse to rotate

See also

SN1 reaction: Substitution of Cl and tert-Butanol
SN2 reaction: substitution of Cl and methanol

References

  1. ChiLe Web Site

Proteopedia Page Contributors and Editors (what is this?)

Veronika Pelekhov, Joel L. Sussman, Jaime Prilusky

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