ORGO- ester formation with KOH + alcohol?????

[Tina324]

---

Members do not see this ad.

Hii,

can someone explain the mechanism by which a carboxylic acid reacts with KOH/alcohol to form an ester...i've never learned this reaction before. Is KOH always involved, or just any strong base?

Thanks!!

 

[Orgodox]

Lets call the alcohol OR. The O from OR attacks the carbonyl carbon and the double bond swings up to become a negative charge on the Oxygen previously double bonded. Now that negative charge kicks down to reform the double bond and kicks off the OH from the carboxylic acid.
The reason KOH is used is so we wont get many different products. In other words even if the O from KOH attacks instead of the O from OR it wont change the starting material it will still be an acid.

 

[Hugh Mannity]

If you have a carboxy acid and KOH it till not be Nucleophilic sub. to a carbonyl. It will be a simple acid-base reaction. It would have to be an ester, anhydride, acyl chloride or amide for that to happen. To form an ester with a carboxy acid and an alcohol it is acid catalyzed.

 

[Mstoothlady2012]

If you have a carboxy acid and KOH it till not be Nucleophilic sub. to a carbonyl. It will be a simple acid-base reaction. It would have to be an ester, anhydride, acyl chloride or amide for that to happen. To form an ester with a carboxy acid and an alcohol it is acid catalyzed.

Exactly!!