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Fischer esterification
Acid-catalyzed reaction of an alcohol and carboxylic acid.
Products of Fischer esterification
Ester and water.
Catalyst used
Sulfuric acid.
Function #1 of sulfuric acid
Protonates the carbonyl oxygen, increasing electrophilicity.
Function #2 of sulfuric acid
Acts as a dehydrating agent.
Why use excess reactant in esterification
To shift equilibrium toward products.
Is Fischer esterification reversible
Yes.
Why wash with water during workup
To remove acids and water-soluble impurities.
Why wash with NaHCO3
To neutralize excess carboxylic acid and sulfuric acid.
What gas forms when NaHCO3 reacts with acid
CO2.
Why wash with brine (NaCl)
To remove water.
Why dry with Na2SO4
To remove residual moisture.
IR evidence of successful esterification
Ester C=O present and alcohol OH absent.
IR evidence of incomplete reaction
Alcohol OH still present.
Ethanol + benzoic acid forms what ester
Ethyl benzoate.
Propyl acetate is formed from what reactants
Propanol and acetic acid.
Ester naming rule
Alkyl group from alcohol + carboxylate from acid.