Preparations of Carboxylic Acids

Chapter  19: Carboxylic Acids

Preparations of Carboxylic Acids
(overview)
 
 
preparations of carboxylic acids

Carbonation of Grignard Reagents, RMgX, by CO2
reaction of RMgX with CO2
Reaction usually in Et2O or THF followed by H3O+ work-up
Reaction type:  Nucleophilic Addition

Summary

Related Reactions
NUCLEOPHILIC ADDITION OF RMgX TO CARBON DIOXIDE
Step 1:
The nucleophilic C in the Grignard reagent adds to the electrophilic C in the polar carbonyl group, electrons from the C=O move to the electronegative O creating an intermediate magnesium carboxylate complex.
addition of Grignard reagent to an aldehyde
Step 2:
This is the  work-up step, a simple acid/base reaction. Protonation of the carboxylate oxygen creates the carboxylic acid product from the intermediate complex.

 

 Hydrolysis of Nitriles

Hydrolysis of RCN to RCO2H

Reaction type : Nucleophilic Substitution then Nucleophilic Addition then  Nucleophilic Acyl Substitution !

Summary

Oxidation of Primary Alcohols
(review Chapter 15)
oxidation of primary alcohols
Reaction type: Oxidation - reduction

Summary


Related Reactions

Oxidation of Aldehydes
oxidation of aldehydes
Reaction type: Oxidation - reduction

Summary


Related Reactions

Oxidation of Alkyl Benzenes
(review of Chapter 11)

oxidation of benzylic CH
Reaction type: Oxidation

Summary:

Question
Why don't 3o alkyl aromatic substituents get oxidized ? they lack any benzylic hydrogens