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10 chem 233 esterification 2011 SPRING

10 chem 233 esterification 2011 SPRING - Esterification...

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4/27/11 1 Esterification Laboratory 8 Esters Volatile esters typically smell ”fruity”
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4/27/11 2 Fisher esterification Conversion of a carboxylic acid and an alcohol to an ester under acid catalysis This is a condensation reaction- 2 molecules make one molecule, and something is lost (H 2 O) Reaction is in equilibrium and does not go to completion Mechanism
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4/27/11 3 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 CH 2 Cl 2 3. Extract with H 2 O Extract with NaHCO 3 CH 2 Cl 2 CH 2 Cl 2 H 2 O HCl H 2 O H 2 O Purification of product and starting material 1. Vacuum filter 2. Wash with cold water 3. Air dry 4. Obtain mass and MP 1. Dry over MgSO 4 2. Gravity filter 3. Evaporate solvent 4. Distill 5. Obtain mass Methyl benzoate Benzoic acid • The entire procedure must be finished in one lab session • Be well organized
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