Organic Acidity

Acidity Factors: Stabilizing the conjugate base ($$\text{A}^-$$) increases acid strength.

Effects: $$-I, -M$$ , high $$s$$ -character increase acidity; $$+I, +M$$ decrease acidity.

• Hybridization Acidity Order:

$$sp \text{ (50\% } s) > sp^2 \text{ (33\% } s) > sp^3 \text{ (25\% } s)$$

• Acidity Order:

$$\text{RCOOH} > \text{H}_2\text{CO}_3 > \text{ArOH} > \text{H}_2\text{O} > \text{ROH} > \text{HC}\equiv\text{CH} > \text{NH}_3 > \text{CH}_2\text{=CH}_2 > \text{CH}_4$$