Question

What is the appropriate catalyst to use?

Fischer Esterification:

Enter the synthesis lab [left-hand desk]. Click on Esterification on the chalkboard.

Choose the starting reagents: 2-phenylacetic acid and ethanol.

Build the experimental setup; you'll need to heat the flask. Add the appropriate catalyst from the reagent bottles.

You will monitor the reaction on the chalkboard and with TLC.

Note the time on the laboratory clock. Start the reaction by turning on the stir plate. Advance the laboratory clock by an interval of 1 minute and run another TLC plate and check the chalkboard. Save every TLC plate that you run.

Continue to advance the clock in 5-minute intervals. Run a TLC plate and check the chalkboard at each interval. You may choose to sample at less frequent intervals if the reaction seems to be proceeding slowly by clicking on the laboratory clock to advance it. Note the time that the reaction is complete.

Clean up.

In preparation for the quiz, draw the structures of the starting reagent and the final product. Have available your TLC screenshots, and the reaction time you were asked to record.

Homework Answers

Answer #1

Fischer Esterification
Fischer-Speier Esterification

The Lewis or Brønstedt acid-catalyzed esterification of carboxylic acids with alcohols to give esters is a typical reaction in which the products and reactants are in equilibrium.

The equilibrium may be influenced by either removing one product from the reaction mixture (for example, removal of the water by azeotropic distillation or absorption by molecular sieves) or by employing an excess of one reactant.

Mechanism of the Fischer Esterification

Addition of a proton (e.g.: p-TsOH, H2SO4) or a Lewis acid leads to a more reactive electrophile. Nucleophilic attack of the alcohol gives a tetrahedral intermediate in which there are two equivalent hydroxyl groups. One of these hydroxyl groups is eliminated after a proton shift (tautomerism) to give water and the ester.

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