Why when i add #NaOH# to 1 it give 2 and not 3 ?

(1)enter image source here

(2)enter image source here

(3)enter image source here

Carboxylic acid a more acid than alcool so why i have this result ?

1 Answer
Apr 23, 2017

It could be explained by steric hindrance.


In this case I would question the original question premise. A carboxylate ion is much more stable than the corresponding alkoxide ion because of the existence of resonance structures for the carboxylate ion which disperse its negative charge. https://www.britannica.com/science/carboxylic-acid

Thus, #3 would be the expected result.

To argue for steric hindrance, the ability of the molecule to form an ion that will essentially be "balanced" by a free #Na^+# ion, as well as the (slight) relative difference in "space" around the #H# for the #OH^-# to get into both indicate spatial interference outweighing functional group relative reactivity.

Thus, the alcohol group would more susceptible to reaction in this molecule. However, as stated initially – the stability of the carboxylate ion compared to the alkoxide ion would most likely result in the last structure, not the second one.