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Orgo Lab Esterification

Submitted by bthoole on Tue, 11/13/2018 - 21:06

In this lab, 1-propyl propionate was synthesized through the esterification of 1-propanol and propionic acid to get a percent yield of 19.81%. The product was assessed for smell and analyzed using IR spectroscopy. The smell of esters is usually something fruity and is a stark contrast to its alcohol and carboxylic acid components, which typically have an unpleasant odor. The carboxylic acid and alcohol are the reactants in the mixture, with the sulfuric acid serving as a catalyst. The reactants create an ester and water in a process known as Fischer esterification. This is a seemingly simple reaction where the carbon and hydroxyl group bond is broken in the carboxylic acid and a new bond is formed between that carbon on the carboxylic acid and the carbon chain bonded to the hydroxyl group on the alcohol. Protonation of the carbonyl carbon of the carboxylic acid makes it a better electrophile which undergoes 1,2 addition by the alcohol and a proton from the alcohol is transferred to a hydroxyl group. 1,2 elimination leads to a protonated ester before it is later deprotonated.

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