10 chem 233 esterification 2011 SPRING

10 chem 233 esterification 2011 SPRING - Esterification...

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Click to edit Master subtitle style 4/27/11 Esterification Laboratory 8
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4/27/11 Esters Volatile esters typically smell ”fruity”
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4/27/11 Fisher esterification Ø Conversion of a carboxylic acid and an alcohol to an ester under acid catalysis Ø This is a condensation reaction- 2 molecules make one molecule, and something is lost (H2O) Ø Reaction is in equilibrium and does not go to completion R OH O HO R 1 R O O R 1 H 2 O H + +
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4/27/11 Mechanism OH O OH OH H O O Me Me OH sulfuric acid HO Me OH O H O Me H OH 2 O H O Me O O H Me proton transfer OH O O Me OH sulfuric acid
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4/27/11 Isolation flowchart Benzoic acid Methanol Methyl benzoate Sulfuric acid Methanol Sulfuric acid Benzoic acid Methyl benzoate Methyl benzoate Benzoic acid Sodium benzoate 1. Reflux 2. Cool and dilute with CH2Cl2 3. Extract with H2O Extract with NaHCO3 CH2Cl2 CH2Cl2 H2O HCl H2O H2O
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4/27/11 Purification of product and starting material 1. Vacuum filter 2. Wash with cold water 3. Air dry 4. Obtain mass and MP
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This note was uploaded on 04/27/2011 for the course CHEM 233 taught by Professor Staff during the Spring '08 term at University of Illinois, Urbana Champaign.

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10 chem 233 esterification 2011 SPRING - Esterification...

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