Synthesis Of Esters

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Synthesis Of Esters

  1. 1. Synthesis of Esters Nucleophilic Acyl Substitution
  2. 2. Uses of Esters <ul><li>Used in perfume making </li></ul><ul><li>Used as food taste enhancers </li></ul><ul><li>Used as solvent of other compounds </li></ul><ul><li>Used as fuel </li></ul>
  3. 3. Reagents <ul><li>Carboxylic Acid </li></ul><ul><li>Alcohol </li></ul>
  4. 6. Procedure <ul><li>Measure prescribed amts of reagents in a round bottom quick fit flask </li></ul><ul><li>Add 2-3 drops of conc. Sulfuric acid </li></ul><ul><li>Reflux for 45-60 minutes </li></ul>
  5. 7. Procedures cont’d. <ul><li>Transfer cooled mixture to a separatory funnel </li></ul><ul><li>Rinse flask with water then add to sep. funnel until volume is twice that of organic layer </li></ul><ul><li>Shake then allow to stratify </li></ul><ul><li>Add NaCl soln to hastes separation </li></ul><ul><li>Add NaHSO4 to neutralize acid </li></ul>
  6. 8. Procedures cont’d <ul><li>Collect organic layer and dry with anhydrous Sodium Sulfate </li></ul><ul><li>Distill using dry glassware </li></ul>
  7. 9. Overall Reaction
  8. 10. Mechanism <ul><li>Nucleophilic Acyl Substitution </li></ul>
  9. 13. note: <ul><li>Esterification is equilibrium sensitive thus the need for excess reagents </li></ul><ul><li>Esters hydrolyze in the presence of water </li></ul>

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