Question
Explain the acidic nature of carboxylic acids.
✓
Answer
Acidic nature of carboxylic acids:
- The carboxyl group (–COOH) imparts an acidic character to carboxylic acids.
- A carboxyl group is made of –OH group bonded to a carbonyl group.
- In aqueous solution, the H atom in OH of carboxyl group dissociates as proton and carboxylate ion is formed as the conjugate base,
$\begin{array}{cc}
\phantom{.}\ce{O}\phantom{......................}\ce{O}\phantom{...........}\\
\phantom{.}||\phantom{......................}||\phantom{...........}\\
\ce{\underset{\text{Carboxylic acid}}{R - C -OH} + H2O ⇌ \underset{\text{Carboxylate ion}}{R - C - O-} + H3O+}
\end{array}$ - Carboxylate ion is resonance stabilized by two equivalent resonance structures as shown below.
- Carboxylate ion has two resonance structures (I) and (II) and both of them are equivalent to each other.
- This gives good resonance stabilization to carboxylate ion, which in turn gives an acidic character to carboxylic acids.
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