Resonance effect in carboxylic acid​

Resonance decreases reactivity because it increases the stability of the molecule. The reason why resonance is decreasing the reactivity of the carboxylic acid is because moving the electrons causes the carbonyl carbon to become less partially positive (which makes the carboxylic acid more stable)

At 1:55, how is resonance decreasing reactivity? Kaplan book says that resonance in carboxylic acid derivates increases stability of the product which increases reactivity.

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Catalina Villafane

3 years ago

Posted 3 years ago. Direct link to Catalina Villafane's post “Resonance decreases reactivity because it increase...”

Resonance decreases reactivity because it increases the stability of the molecule. The reason why resonance is decreasing the reactivity of the carboxylic acid is because moving the electrons causes the carbonyl carbon to become less partially positive (which makes the carboxylic acid more stable). When you stabilize the carboxylic acid by making the carbonyl carbon less positive, you are decreasing its ability to be an electrophile in a reaction (in other words, you are making the molecule less reactive due to the increase in stability from the resonance).

Reactivity and stability are two opposing concepts. The more stable a molecule is, the less it wants to react. A decrease in stability results in an increase in reactivity and an increase in stability causes a decrease in reactivity. Think of it this way: a molecule always wants to be in it's most stable form. If it's not stable, it is going to want to react in order to stabilize itself. If it's already stable, it doesn't need to react.