Reaction of Grignard reagent with ethyl acetate

Grignard reagent is an extremely important reagent in organic synthesis, and its reaction with ethyl acetate contains many subtleties.

Grignard reagents are generally prepared by reacting halogenated hydrocarbons with metallic magnesium in anhydrous ether or tetrahydrofuran solvents. When Grignard reagent meets ethyl acetate, first, the hydrocarbon negative ions in Grignard reagent will launch a nucleophilic attack on the carbonyl carbon in ethyl acetate. During this process, the original electron cloud distribution of carbonyl carbon changes, the π bond in the carbon-oxygen double bond is opened, and the electrons are biased towards the oxygen atom, forming a negatively charged intermediate.

Then, the intermediate is unstable, and the ethoxy group leaves as a leaving group to form a ketone. However, the activity of the Grignard reagent is quite high, and the generated ketone will continue to react with the Grignard reagent. The anion of the hydrocarbon group in the Grignard reagent once again attacks the carbonyl carbon of the ketone, forming a new negatively charged intermediate.

Subsequently, hydrolyzed under acidic conditions, this intermediate binds to protons, and finally produces the corresponding alcohol. The alcohol produced by this reaction has a unique structure, and its structure depends on the structure of the hydrocarbon group in the Grignard reagent. The reaction of Grignard reagent with ethyl acetate provides an extremely effective method for the construction of carbon-carbon bonds and the synthesis of specific alcohols for organic synthesis. It is widely used in the field of organic chemistry and helps to synthesize many complex organic compounds.