Explain the mechanism of the following reaction: the addition of a Grignard reagent to the carbonyl group of a compound.

Question

08-03-2025
Chemistry

High School

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Explain the mechanism of the following reaction: the addition of a Grignard reagent to the carbonyl group of a compound.

Answer :

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RayneBliss RayneBliss · Answer 1 · 2024-09-23T20:25:45-04:00

Final answer:

The addition of Grignard reagents to carbonyl compounds involves forming an acid-base complex, followed by nucleophilic attack on the carbonyl carbon, resulting in a new carbon-carbon bond and the formation of an alcohol.

Explanation:

The mechanism of reaction for the addition of Grignard reagents to carbonyl compounds is a crucial concept in organic chemistry that involves several steps, ultimately resulting in the formation of a new carbon-carbon bond. Initially, the Grignard reagent interacts with the carbonyl compound to form an acid-base complex, where the magnesium halide (MgX, where X is usually Br or Cl) of the Grignard reagent acts as a Lewis acid by accepting a pair of electrons from the carbonyl oxygen. This interaction increases the partial positive charge on the carbonyl carbon, making it more susceptible to nucleophilic attack.

Following this, the carbon part of the Grignard reagent acts as a nucleophile and attacks the electrophilic carbonyl carbon, leading to the formation of a tetrahedral magnesium alkoxide intermediate. To complete the reaction, an acidic aqueous solution is added, converting the intermediate into an alcohol and regenerating the MgX compound in a different form (HOMgX). This mechanism is fundamental in organic synthesis, allowing for the creation of a wide array of alcohol derivatives from simple carbonyl precursors.