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ORGANIC CHEMISTRY
Louella Mariz C. Dominguez
BSMT Irreg.

FISCHER ESTERIFICATIONORFISCHER
SPEIER ESTERIFICATION
-is a special type
ofesterificationbyrefluxingacarboxylic
acidand an alcoholin the
presence of anacidcatalyst.
- The reaction was first described byEmil
Fischerand Arthur Speier in 1895

(9 October 1852 15 July 1919)

Germanchemistand1902 recipient
of theNobel Prize in Chemistry
Chemical reactions and concepts
are named after him:
Fischer indole synthesis
Fischer projection
Fischer oxazole synthesis
Fischer peptide synthesis
Fischer phenylhydrazine and oxazone
reaction
Fischer reduction
Fischer-Speier esterification
Fischer glycosidation
Emil
Fischer

FISCHER ESTERIFICATION

COMMONLY USED CATALYSTS FOR A

FISCHER ESTERIFICATION

1)sulfuric acid (H2SO4)

2)tosic acid (CH3C6H4SO3H), and
3)Lewis acidssuch
asscandium(III) triflate

OVERVIEW

Fischer esterification is an example ofnucleophilic acyl

substitutionbased on the electrophilicity of
thecarbonylcarbon and the nucleophilicity of an alcohol.

Thereaction mechanism for this reaction has several steps:

Proton transfer from acid catalyst tocarbonyloxygen
increaseselectrophilicityof carbonyl carbon.
The carbonyl carbon is then attacked by thenucleophilic oxygen
atom of the alcohol
Proton transfer from theoxonium ionto a second molecule of the
alcohol gives an activated complex
Protonation of one of the hydroxyl groups of the activated
complex gives a new oxonium ion.
Loss of water from this oxonium ion and subsequent
deprotonation gives theester.

A GENERIC MECHANISM FOR AN ACID

FISCHER ESTERIFICATION IS SHOWN
BELOW:

USES

Flavorings
Perfuming Agents
Medicines
Wine/ Alcohol

SOURCES OF ERROR IN
ESTERIFICATION
Water-it quenches the esterification process
This is especially true if you're using an acid halide /
anhydride.
If you're using acarboxylic acidandalcoholwith an
acid catalyst, the water formed needs to be removed
as it will compete with the alcohol, reforming the acid.
This can be done with drying agents, sieves, or, since
these reactions are conducted at elevated
temperatures, using a Dean-Stark apparatus and
toluene as the solvent.

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listening