Carboxylation, of Grignard reagents

The addition of a Grignard reagent to carbon dioxide gives the salt of the corresponding carboxylic acid, which on acidification yields the free carboxylic acid. 

The synthesis of 2-methylbutanoic acid (Expt 5.129) is illustrative of the method. Other organometallic reagents undergo a similar carboxylation reaction, and examples of the use of organolithium and organosodium reagents are included in the section on the synthesis of aromatic carboxylic acids (Section 6.13.3, p. 1069). 

(1) 2-Chlorobutane is employed in preference to the bromide because it is cheaper and the yield of acid is slightly higher. 

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SYNTHESIS OF CARBOXYLIC ACIDS BY THE CARBOXYLATION OF GRIGNARD REAGENTS... 

Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents... 

Overall the carboxylation of Grignard reagents transforms an alkyl or aryl halide to a carboxylic acid in which the carbon skeleton has been extended by one carbon atom... 

Show how to synthesize carboxylic acids from oxidation of alcohols and aldehydes. Problems 20-36, 39, and 44 carboxylation of Grignard reagents, oxidative cleavage of alkenes and alkynes, hydrolysis of nitriles, and oxidation of alkylbenzenes. 

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