grignard reagent

A Grignard Reagent is an alkyl- or aryl- magnesium halide. It is important in the synthesis of carbon-carbon bonds. Grignard reagents undergo reactions with compounds containing carbonyl groups. These reactions create alcohols. Victor Grignard won the 1912 Nobel Prize in Chemistry for his discovery of Grignard reagents. Grignard reagents are formed by reacting alkyl or aryl halides with organomagnesium metal, conferring a negative charge on the terminal carbon, a rare occurrence. Bromides are most often used, as they work the fastest and are readily available among halides (iodide and chloride are also used, while fluoride is generally unreactive towards organomagnesium compounds. The Grignard reaction is exothermic and because of a oxide layer present on the magnesium, the start of the reaction is sometimes delayed. In reactions involving Grignard reagents, it is important to ensure that no water is present, which would otherwise cause the reagent to rapidly decompose. Thus, most Grignard reactions occur in solvents such as anhydrous ether or tetrahydrofuran, because the oxygen of these solvents stabilizes the magnesium reagent. The reagent may also react with oxygen present in the atmosphere, inserting an oxygen atom between the carbon base and the magnesium halide group. Thus, many of these reactions are carried out in nitrogen or argon atmospheres.

Grignard Reagent

See also