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ESTERIFICATION AND HYDROLYSIS
ESTERIFICATION AND HYDROLYSIS Experiment #1: Methyl Benzoate by Fisher Esterification Post – Lab Organic Chemistry II Lab – Section 7515 February 25, 2004 INTRODUCTION The Fischer esterification reaction reaches equilibrium after a few hours. This equilibrium can be shifted by adding more of the acid or of the alcohol. The mechanism of the reaction involves initial protonation of the carboxyl group, followed by attack by nucleophilic hydroxyl, a proton transfer, and finally loss of water followed by loss of the catalyzing proton to give ester. All these steps are also reversable. The purpose of this experiment is to obtain methyl benzoate through fisher esterification by using benzoic acid, methanol, and concentrated sulfuric acid. EXPERIMENTAL PROCEDURE 10g of pre-weighed benzoic acid and 25ml of methanol were placed into the 125ml round bottomed flask. 3ml of concentrated sulfuric acid was added to the flask very carefully after the mixture cooled off (in the ice bath) to approximately room temperature and the whole mixture was then swirled. After the reflux condenser was attached, the boiling chip was added, the mixture was refluxed for approximately 1 hour. The solution was then cooled and was poured into a separatory funnel that contained 50ml of water. The flask was rinsed with 35ml of ethyl ether, and this was then added to the separatory funnel. The separatory funnel was shaken well and the water layer (containing sulfuric acid and methanol) was drained off. The ether in separatory funnel was washed with 25ml of water and then with 25ml of 0.5M sodium bicarbonate (to remove unreacted benzoic acid). The funnel was shaken well again with frequent release of pressure (inverting the separatory funnel and opening the stopcock) until no reaction was visible and the bicarbonate layer was drained off into a beaker. The ether layer in separatory funnel was washed with saturated sodium chloride solution and dried with a... Please login to view comments from other users.
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