This document discusses the synthesis of esters via nucleophilic acyl substitution. Esters are used in perfumes, foods, solvents, and fuels. The procedure involves refluxing a carboxylic acid and alcohol with sulfuric acid, then separating the organic layer containing the ester product. The overall reaction is an esterification via nucleophilic acyl substitution.

1. Synthesis of Esters Nucleophilic Acyl Substitution

2. Uses of Esters Used in perfume making Used as food taste enhancers Used as solvent of other compounds Used as fuel

3. Reagents Carboxylic Acid Alcohol

6. Procedure Measure prescribed amts of reagents in a round bottom quick fit flask Add 2-3 drops of conc. Sulfuric acid Reflux for 45-60 minutes

7. Procedures cont’d. Transfer cooled mixture to a separatory funnel Rinse flask with water then add to sep. funnel until volume is twice that of organic layer Shake then allow to stratify Add NaCl soln to hastes separation Add NaHSO4 to neutralize acid

8. Procedures cont’d Collect organic layer and dry with anhydrous Sodium Sulfate Distill using dry glassware

9. Overall Reaction

10. Mechanism Nucleophilic Acyl Substitution

13. note: Esterification is equilibrium sensitive thus the need for excess reagents Esters hydrolyze in the presence of water