High school11 min

Carboxylic acids, esters and soaps

Write an esterification, name the ester without swapping its two halves, calculate a yield, and know why saponification, unlike it, goes to completion.

The essentials

1

The carboxylic acid, a weak acid

The COOH\ce{-COOH} group combines a C=O\ce{C=O} and an OH\ce{-OH} on the same carbon. In water it gives up its proton only partially: RCOOH+HX2ORCOOX+HX3OX+\ce{R-COOH + H2O <=> R-COO^- + H3O+} For most of these acids, the pKa\text{p}K_a of the RCOOH/RCOOX\ce{R-COOH}/\ce{R-COO^-} couple lies between 44 and 55: the equilibrium lies far to the left.
2

Esterification and hydrolysis

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3

Rate and yield: two separate levers

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4

Naming an ester

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5

Saponification

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ƒWrite my own sheetOr start from a blank page: rewriting a concept in your own words is how it sticks.