Organic Chemistry · Chapter 8: Carboxylic Acids

Question

Substituents on carbon atoms near a carboxyl group influence an____d therefore affect acidity.

Answer

Substituents on carbon atoms near a carboxyl group influence anion stability and therefore affect acidity.
Substituents on carbon atoms near a carboxyl group influence anion stability and therefore affect acidity.
Examples: Groups like –NO2 or halides are electron-withdrawing and increase acidity. In contrast, –NH2 or –OCH3 are electron-donating groups that destabilize the negative charge, decreasing the acidity of the compound.
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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More cards in Chapter 8: Carboxylic Acids

A carboxylic acid contains both a ____ group, bonded to the same carbon.

Carboxylic acids are named by adding the suffix ____ to the parent root when the carboxylic acid is the highest-priority functional group.

The same common-name prefixes are used for both aldehydes and carboxylic acids: ____ for three.

Cyclic carboxylic acids are named by listing the cycloalkane with the suffix ____.

Salts of carboxylic acids are named beginning with the cation, followed by the name of the acid with the ending ____ replacing – oic acid .

____, followed by the name of the acid with the ending – oate replacing – oic acid .

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