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Chapter 40 Esterification. Synthesis of n -Butyl Acetate by Azeotropic Distillation of Water

Chapter 40 Esterification. Synthesis of n -Butyl Acetate by Azeotropic Distillation of Water. Purpose. In this experiment acetic acid is esterified with butanol in the presence of an acid catalyst in an azeotropic distillation mode.

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Chapter 40 Esterification. Synthesis of n -Butyl Acetate by Azeotropic Distillation of Water

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  1. Chapter 40 Esterification. Synthesis of n-Butyl Acetate by Azeotropic Distillation of Water

  2. Purpose • In this experiment acetic acid is esterified with butanol in the presence of an acid catalyst in an azeotropic distillation mode. • The product is isolated simply by withdrawing it from reaction flask with a Pasteur pipette, leaving the catalyst behind .

  3. Reaction Mechanism • The mechanism involves initial protonation of CO2H group, attack of the nucleophilic OH, a proton transfer, and loss of H2O followed by loss of the catalyzing proton to give ester.

  4. Comments • Follow pp. 559-560 (microscale). • Follow the lab handout for all experimental procedures. Note ‘fruity’ fragrance of the final product (use wafting, do not inhale!). • Perform IR analysis of the product. • Calculate yield. High to moderate yields should be achieved. (Moles Product / Moles Starting Material) x 100 = % Yield

  5. Safety • Flammable reagents are used in this experiment, keep away from open flame. • Acetic acid is corrosive, avoid contact with skin and eyes. • n-Butyl acetate can cause irritation of eyes, upper respiratory system and skin.Potential symptoms of overexposure are headache, drowsiness, narcosis. Do not inhale, avoid contact with skin and eyes.

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