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Related Concept Videos

Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

2.4K
Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
2.4K
Esters to Alcohols: Grignard Reaction01:08

Esters to Alcohols: Grignard Reaction

4.4K
The reaction of an ester with a Grignard reagent, followed by hydrolysis of the magnesium alkoxide salt in aqueous acid, yields a tertiary alcohol. In the case of formate esters, secondary alcohols are formed.
The reaction requires two equivalents of the Grignard reagent and introduces two identical alkyl groups, derived from the Grignard reagent, bonded to the hydroxyl-bearing carbon of the alcohol.
The reaction follows the typical nucleophilic acyl substitution mechanism. The Grignard...
4.4K
Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

4.8K
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...
4.8K
Alcohols from Carbonyl Compounds: Grignard Reaction02:00

Alcohols from Carbonyl Compounds: Grignard Reaction

5.8K
Grignard reagents are one of the most commonly used reagents used to synthesize alcohols from carbonyl compounds. Grignard reagents are organomagnesium halides with a highly polar carbon–magnesium bond. Due to the partial ionic nature of the C–Mg bond, the carbon functions as a strong nucleophile and attacks electrophiles like carbonyl carbon.
Magnesium from the reagent coordinates with carbonyl oxygen, further reducing the carbonyl carbon's electron density. Thus, the...
5.8K
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

15.7K
Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
15.7K
E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

10.6K
SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
10.6K

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Updated: Sep 9, 2025

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
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Are Grignard Reactions in Deep Eutectic Solvents Interface-Driven?

Iva Manasi1,2, Marco Bortoli3, Daniel T Bowron4

  • 1Department of Physics, University of Bristol, Tyndall Avenue, Bristol, BS8 1TL, United Kingdom.

Angewandte Chemie (International Ed. in English)
|September 2, 2025
PubMed
Summary
This summary is machine-generated.

Deep eutectic solvents (DES) enable organometallic additions to ketones at room temperature. This study reveals DES poor solvation of ketones and interface localization of reagents enhance reactivity and stability.

Keywords:
Biphasic systemsGreen chemistryInterfacial reactionsNon‐volatile solventsSolvophobic effect

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry
  • Materials Science

Background:

  • Organolithium and organomagnesium additions to ketones are typically performed under inert atmospheres and low temperatures due to high reactivity.
  • Recent advancements show deep eutectic solvents (DES) facilitate these reactions under ambient conditions (benchtop, air, room temperature).

Purpose of the Study:

  • To investigate the mechanism behind the enhanced reactivity and stability of organometallic additions to ketones in a choline chloride:glycerol (ChCl:Gly) DES.
  • To understand the role of the DES in facilitating reactions typically requiring stringent conditions.

Main Methods:

  • Experimental techniques including liquid diffraction, neutron reflectometry, and Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Interfacial tension measurements and computational modeling (molecular dynamics simulations).
  • Investigation of acetophenone as the ketone substrate in a (1:2) ChCl:Gly DES.

Main Results:

  • The ChCl:Gly DES acts as a poor solvent for acetophenone, leading to its accumulation at the solvent interface or partitioning into an organic solvent.
  • Molecular dynamics simulations showed Grignard reagents prefer localization at the interface in a biphasic DES/organic solvent system.
  • These interfacial phenomena explain the enhanced reaction efficiency and reduced decomposition of organometallic reagents.

Conclusions:

  • The poor solvation of ketones and preferential localization of organometallic reagents at the interface in DES systems are key to enabling benchtop reactions.
  • Stirring is necessary due to the interfacial nature of the reaction, and the observed phenomena protect organometallic reagents from rapid decomposition.
  • Deep eutectic solvents offer a promising alternative for performing sensitive organometallic reactions under milder, more accessible conditions.