[omegasynthesis999]

Carboxylic acids are more stable and less reactive than an ester, therefore why is it possible to convert a carboxylic acid to an ester?

Is it because difference in stability and reacitvity is slim and with harsh conditions (i.e. acid, alcohol, and acid in a fischer esterification) you are able to overcome the associated problems?

Thanks.

[seanifred]

i think you just answered your own question

the reaction is acid-catalyzed, which answers the question right there

the protonation of the carbonyl makes the carbonyl carbon a more reactive electrophile, thus attracted the alcohol in solution

then the molecule looks like a di-ol ether, which is easily dehydrated by the acidic solvent

this replaces the acid used in protonation

so the acid in solution is a true catalyst as it is always remade after reaction

[spirochete]

This is also one of the many applications of le chatlier's principle in organic chem.

Amides can also be hydrolyzed to esters under acid or base conditions which is even more uphill in reactivity.  Although in basic solution something happens which ultimately helps pull the reaction to the right.  If you want draw out the full mechanism and you'll see what I'm referring to.

[spirochete]

Should say "acid" in place of ester in the above post.  There seems to be something wrong with the editing function.