How does a Gilman reagent react with carbonyl compounds?

A Gilman reagent reacts with carbonyl compounds to form a new carbon-carbon bond, resulting in an alcohol.

A Gilman reagent, also known as an organocopper reagent, is a type of organometallic compound that is commonly used in organic chemistry. It is named after the American chemist Henry Gilman, who first discovered it. The general formula for a Gilman reagent is R2CuLi, where R represents an alkyl or aryl group.

When a Gilman reagent reacts with a carbonyl compound, a nucleophilic addition reaction occurs. The carbonyl compound has a polar double bond between the carbon and oxygen atoms. This makes the carbon atom electrophilic, meaning it is attracted to electron-rich species. The Gilman reagent, being a nucleophile (electron-rich species), is attracted to this electrophilic carbon.

The reaction proceeds with the Gilman reagent attacking the carbonyl carbon, breaking the carbon-oxygen double bond. This results in the formation of a new carbon-carbon bond, with the oxygen atom now having a single bond to the carbon and carrying a negative charge. This negatively charged oxygen atom then abstracts a proton from a solvent molecule, resulting in the formation of an alcohol.

This reaction is particularly useful in organic synthesis as it allows for the formation of new carbon-carbon bonds, which is a key step in the synthesis of many complex organic molecules. It's also noteworthy that Gilman reagents can react with a variety of carbonyl compounds, including aldehydes, ketones, and esters, making them versatile tools in the field of organic chemistry.

In summary, the reaction of a Gilman reagent with a carbonyl compound involves a nucleophilic addition to the carbonyl carbon, resulting in the formation of a new carbon-carbon bond and an alcohol. This reaction is a fundamental process in organic chemistry and is widely used in the synthesis of complex organic molecules.