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Comparing Acidities of Organic Acids

17) Explain why cyanoacetic acid and methoxyacctic acid are more acidic than their correspondingly substituted benzoic acid counterparts.

18) Even though the para position is one carbon farther from the carboxy group than the meta position, p-cyanobenzoic acid is more acidic than m-cyanobenzoic acid. Explain the differences in acidity between p-cyanobenzoic acid and m-cyanobenzoic acid.

19) Explain the differences in acidity between p-methoxybenzoic acid and m-methoxybenzoic acid.

Questions 21-22: Consider the data below to answer the following question(s).
When CO2 is bubbled through an ether solution of benzylmagnesium bromide, and the resulting mixture is acidified, phenylacetic acid is produced. Any unreacted benzylmagnesium bromide is converted to toluene in the acidification step.

20) Write the complete reaction sequence for the process described above.

21) How could you separate phenylacetic acid from toluene.

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Solution Summary

This posting has 5 problems outlining in detail how to tell which compound is more acidic.