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AN INTRODUCTION TO GRIGNARD REAGENTS

The Grignard reagent can therefore serve as a because of the attraction between the slight negativeness of the carbon atom in the Grignard reagent and the positiveness of the carbon in the carbonyl compound.

A typical Grignard reagent might be CH3CH2MgBr.

Review and extend CCBFR from 1C1Y, in particular:
Aldol and Claisen condensations
Alkylation of -keto esters (RCHOCH2CO2R’)
Grignard reactions

The preparation of a Grignard reagent

A typical Grignard reagent might be CH3CH2MgBr.

The reactions between the various sorts of carbonyl compounds and Grignard reagents can look quite complicated, but in fact they all react in the same way - all that changes are the groups attached to the carbon-oxygen double bond.

The mechanisms for these reactions aren't required by any UK A level syllabuses, but you might need to know a little about the nature of Grignard reagents.

The preparation of a Grignard reagent

Everything must be perfectly dry because Grignard reagents react with water.

So far, we have built a small repertoire of reactions that canbe used to convert one functional group to another. We havebriefly discussed converting alkenes to alkanes; alkanes to alkylhalides; alkyl halides to alcohols; alcohols to ethers,aldehydes, or ketones; and aldehydes to carboxylic acids. We havealso shown how carboxylic acids can be converted into esters andamides. We have yet to encounter a reaction, however, thataddresses a basic question: How do we make CC bonds? Oneanswer resulted from the work that Francois Auguste VictorGrignard started as part of his Ph.D. research at the turn of thecentury.

Grignard noted that alkyl halides react with magnesium metalin diethyl ether (Et2O) to form compounds that containa metal-carbon bond. Methyl bromide, for example, formsmethylmagnesium bromide.

Reactions of Grignard reagents with aldehydes and ketones
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Grignard reagents and carbon dioxide

Grignard reagents such as methylmagnesium bromide aretherefore sources of a nucleophile that can attack the +end of the C=O double bond in aldehydes and ketones.

Grignard reagents and carbonyl compounds

This page looks at the reaction of aldehydes and ketones with Grignard reagents to produce potentially quite complicated alcohols. It is mainly a duplication of the information on these same reactions from a page on Grignard reagents in the section on properties of halogenoalkanes.

The reaction between Grignard reagents and methanal

A Grignard reagent has a formula RMgX where X is a halogen, and R is an alkyl or aryl (based on a benzene ring) group. For the purposes of this page, we shall take R to be an alkyl group.

The reaction between Grignard reagents and other aldehydes

Grignard reagents are made by adding the halogenoalkane to small bits of magnesium in a flask containing ethoxyethane (commonly called diethyl ether or just "ether"). The flask is fitted with a reflux condenser, and the mixture is warmed over a water bath for 20 - 30 minutes.

The reaction between Grignard reagents and ketones

Grignard reagents are our first source of carbanions(literally, "anions of carbon"). The Lewis structure ofthe CH3- ion suggests that carbanions canbe Lewis bases, or electron-pair donors.

1. To introduce basic concepts of organic synthesis:

A Grignard reagent has a formula RMgX where X is a halogen, and R is an alkyl or aryl (based on a benzene ring) group. For the purposes of this page, we shall take R to be an alkyl group.

AN INTRODUCTION TO GRIGNARD REAGENTS - …

This page takes an introductory look at how Grignard reagents are made from halogenoalkanes (haloalkanes or alkyl halides), and introduces some of their reactions.

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