High School

We appreciate your visit to Write a detailed mechanism for the reaction of the Grignard reagent with the ketone or ester to be used in your experiment. This page offers clear insights and highlights the essential aspects of the topic. Our goal is to provide a helpful and engaging learning experience. Explore the content and find the answers you need!

Write a detailed mechanism for the reaction of the Grignard reagent with the ketone or ester to be used in your experiment.

Answer :

The reaction mechanism of a Grignard reagent with an ester consists of a nucleophilic attack by the Grignard's alkyl group on the ester's carbonyl carbon, replacement of the ester's OR' group with an alkyl group to form a ketone, a second attack by the Grignard on the ketone, and an acid work-up to give a tertiary alcohol.

Grignard reagents are widely used in organic chemistry for the synthesis of alcohols, and their reaction with esters can produce tertiary alcohols. The mechanism for the reaction between a Grignard reagent and an ester involves multiple steps:

  1. Nucleophilic Attack: The first step is nucleophilic attack, where the Grignard reagent's alkyl group (R-) acts as a nucleophile and attacks the electrophilic carbon atom of the carbonyl group (C=O) in the ester.
  2. The OR' group (leaving group) of the ester is replaced by the alkyl group from the Grignard reagent, resulting in a ketone intermediate.
  3. The newly formed ketone is then immediately attacked by another molecule of the Grignard reagent, resulting in an alkoxide intermediate.
  4. Finally, the reaction is completed with an acid work-up step (usually aqueous acid) to protonate the alkoxide, thus forming the desired tertiary alcohol. The two identical alkyl groups attached to the alcohol carbon come from the Grignard reagent, granting the molecule its tertiary status if the R group of the ester is also a carbon group.

It is important to note that esters react with two equivalents of the Grignard reagent to give the tertiary alcohol after the intermediate ketone is formed.

Thanks for taking the time to read Write a detailed mechanism for the reaction of the Grignard reagent with the ketone or ester to be used in your experiment. We hope the insights shared have been valuable and enhanced your understanding of the topic. Don�t hesitate to browse our website for more informative and engaging content!

Rewritten by : Barada