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Esters

Reactivity of Esters

Transesteri cation
Last updated: 17:40, 25 Jun 2014

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Transesteri cation is the conversion of a carboxylic acid ester into a different carboxylic acid ester.

Introduction
When in ester is placed in a large excess of an alcohol along with presence of either an acid or a base there can be an
exchange of alkoxy groups. The large excess of alcohol is used to drive the reaction forward. The most common
method of transesteri cation is the reaction of the ester with an alcohol in the presence of an acid catalyst eg:

This reaction has the following mechanism:

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Since both the reactants and the products are an ester and an alcohol, the reaction is reversible and the equilibrium
constant is close to one. Consequently, the Le Chateliers principle has to be exploited to drive the reaction to
completion. The simplest way to do so is to use the alcohol as the solvent as well.

General reaction

Example 1:

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Mechanism in basic conditions

Nucleophilic attack by an alkoxide

2) Leaving group removal

Mechanism in acidic conditions

1) Protonation of the carbonyl by the acid. The carbonyl is now activated toward nucleophilic attack.

2) Nucleophilic attack on the carbonyl

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3) Proton transfer

4) Removal of the leaving group

5) Deprotonation

Contributors
Prof. Steven Farmer (Sonoma State University)
Gamini Gunawardena from the OChemPal site (Utah Valley University)

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The Hydrolysis of Esters

Synthesis of Esters

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The Hydrolysis of Esters
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Esters can be converted aldehydes using diisobutylaluminum hydride (DIBAH).
Esters can be reduced to 1 alcohols using LiAlH4

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