Grignard Lab

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Nucleophilic Carbon-Formation and Reaction of a Grignard Reaction
03/03/2014

Nucleophilic Carbon-Formation and reaction of a Grignard reagent

Abstract: In this experiment, phenyl benzoate was made in order to react it with methyl benzoate in order to produce the compound triphenylmethanol via a grignard reaction. There was a 37.2% yield of triphenylmethanol, and the melting point obtained was 161-163°C.

Introduction: Grignard reagents are usually formed when alkyl halides and magnesium react together. The carbon and magnesium have a very large difference in electronegativity. This allows the carbon to withdraw the electron density from magnesium through the process of induction.1 Grignard reagents are related to organolithium reagents which are useful and contain carbon atoms that are strongly nucleophilic. They react with a range of carbonyl compounds to make new carbon-carbon bonds. In this lab, phenyl magnesium bromide will be reacted with methyl benzoate to obtain triphenylmethanol which is a grignard reaction.

Mechanism:

Experiment:

Place 0.5g of crushed magnesium turnings into 50 mL round bottom flask; add the stir bar, and 5mL of anhydrous ether. Construct an apparatus for slow addition of reagents and also so the reaction can go into reflux. Make up a solution of 2.4mL of bromobenzene in 5mL of anhydrous ether in a dry flask then add it to the separatory funnel. Add about 0.5mL of bromobenzene of the bromobenzene solution to the mixture of magnesium and ether, with vigorous stirring. Then add another 5mL of anhydrous ether through the condenser as the reaction heats up. The solution made up for bromobenzene, add it into the separatory funnel so the mixture maintains a reflux, but not let it boil very hard. Once all the bromobenzene is added, rinse the separatory funnel with 2mL of anhydrous ether to wash any remaining bromide into the…...

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