Grignard carboxylation co reactant

Overview

Carbon dioxide plus a Grignard reagent gives a carboxylic acid after acidic work-up.

Transformation

Carbon dioxide → Carboxylic acids

Equation

CO2 + R-MgX -> R-CO2MgX; then H3O+ -> R-CO2H

Reagents

Grignard reagent, then dilute acid

Environment

dry ether, then acidic work-up

Reaction class

carboxylation

Mechanism

Grignard carboxylation

Evidence level

textbook core

Scope and limitations

Scope

Carbon dioxide is the one-carbon co-reactant in Grignard carboxylation to carboxylic acids.

Limitations

This record represents the carbon-dioxide co-reactant branch and points to the same carboxylic-acid outcome after acidic work-up.

Related reactions

• Oxidation: Alcohols → Carboxylic acids

  Full oxidation of a primary alcohol gives a carboxylic acid.

• Complete oxidation: Primary alcohols → Carboxylic acids

  Full oxidation of a primary alcohol gives a carboxylic acid.

• Reduction: Carboxylic acids → Primary alcohols

  Reduction of a carboxylic acid gives a primary alcohol.

• Oxidation: Aldehydes → Carboxylic acids

  Oxidation of an aldehyde gives a carboxylic acid.

• Hydrolysis: Nitriles → Carboxylic acids

  Nitriles can be hydrolysed to carboxylic acids, splitting the old aggregate nitrile-to-amide route into a single functional-group conversion.

• Activation for amide formation: Carboxylic acids → Amide chemistry

  Carboxylic acids or activated acid derivatives connect to amide-bond formation.

• Esterification: Carboxylic acids → Esters

  Carboxylic acids react with alcohols to form esters.

• Hydrolysis: Esters → Carboxylic acids

  Hydrolysis converts esters back into carboxylic acid products.

• Chlorination: Carboxylic acids → Acyl chlorides

  PCl5 converts carboxylic acids into acyl chlorides.

• Chlorination with thionyl chloride: Carboxylic acids → Acyl chlorides

  Thionyl chloride converts carboxylic acids into acyl chlorides with sulfur dioxide and hydrogen chloride as by-products.

• Hydrolysis: Acyl chlorides → Carboxylic acids

  Water hydrolyses acyl chlorides to carboxylic acids, releasing hydrogen chloride.

• Carboxylation: Grignard reagents → Carboxylic acids

  Grignard carboxylation gives carboxylic acids after acidic work-up.

• Complete combustion: Alkanes → Carbon dioxide

  Alkanes burn completely in excess oxygen to form carbon dioxide and water.

• Complete combustion: Alcohols → Carbon dioxide

  Alcohols burn completely in excess oxygen to form carbon dioxide and water.

• Combustion: Benzene → Carbon dioxide

  Benzene combusts to carbon dioxide and water and tends to burn with a smoky flame.

• Salt formation: Carboxylic acids → Carboxylate salts

  Carboxylic acids react with bases, carbonates and reactive metals to form carboxylate salts.

References

1. Organic Chemistry: Preparing Carboxylic AcidsJohn McMurry · OpenStax Organic Chemistry · 2023

   Supports dry carbon dioxide reacting with Grignard reagents to form carboxylates that give carboxylic acids after acidic work-up.