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Alkyl Halide Reactions: Carboxylic Acid formation using Alkyl Halides, Mg, and CO2

Alkyl halides (R-X) that are reacted to form Grignard reagents (RMgX) can react with carbon dioxide (CO2) in acidic environments to form carboxylic acids:

Alkyl Halide Reactions: Carboxylic Acid formation using Alkyl Halides, Mg, and CO2 image1.png

This reaction is pretty straight forward; the halogen group is replaced with the carbon atom of the carboxylic acid group. This reaction may be presented in a different way where the alkyl halide has already formed a Grignard reagent by adding Mg. The halogen group can be Cl, Br, or I.

The reaction mechanism is depicted below:

Alkyl Halide Reactions: Carboxylic Acid formation using Alkyl Halides, Mg, and CO2 image2.png

In the first step, the magnesium is added to the molecule and takes its place between the carbon atom and the halogen atom. Then, the electrons from the carbon-magnesium bond attack the carbon dioxide-carbon atom, breaking the carbon-magnesium bond.

In the second step, the electronegative oxygen attacks a nearby H3O+ proton, completing the reaction.