Draw the stepwise mechanism showing electron flow & product formation for the Fi

Question

Draw the stepwise mechanism showing electron flow & product formation for the Fischer esterification of butanoic acid with 1-propanol. Show all intermediates leading to product formation. Draw the stepwise mechanism showing electron flow & product formation for the Fischer esterification of butanoic acid with 1-propanol. Show all intermediates leading to product formation. Draw the stepwise mechanism showing electron flow & product formation for the Fischer esterification of butanoic acid with 1-propanol. Show all intermediates leading to product formation.

Explanation / Answer

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.

Alternative reactions employ coupling reagents such as DCC, preformed esters (transesterification), carboxylic acid chlorides or anhydrides . These reactions avoid the production of water. Another pathway for the production of esters is the formation of a carboxylate anion, which then reacts as a nucleophile with an electrophile (similar reactions can be found here). Esters may also be produced by oxidations, namely by the Baeyer-Villiger oxidation andoxidative esterifications.

propanol    + butanoic acid ====> propyl butanoate  +  water.

C3H7OH(aq) +  C3H7CO2H(aq) ====> C3H7CO2C3H7(aq) + H2O(l)

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