Organic Chemistry · Chapter 8: Carboxylic Acids

Question

The closer the ____ substituent groups are to the carboxyl group, the greater the acidity will be.

Answer

The closer the electron withdrawing substituent groups are to the carboxyl group, the greater the acidity will be.
The closer the electron withdrawing substituent groups are to the carboxyl group, the greater the acidity will be.
Why do carboxylic acids dissociate to a greater extent than do alcohols?
The difference is that the hydroxy substituent of a carboxylic acid is attached to a carbonyl group, whose positively polarized and sp2 -hybridized carbonyl carbon exerts a powerful electron-withdrawing inductive effect. In addition, the carboxylate ion is signifi cantly stabilized by resonance, much as is the enolate ion formed by deprotonation of the -carbon in aldehydes and ketones.

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