In an experiment, triphenylmethanol is prepared using the Grignard reaction. The Grignard reaction involves preparation and reaction of a very nucleophilic organo-magnesium compound. The Grignard reagent is very reactive and is easily destroyed by reaction with atmospheric water, oxygen, or carbon dioxide. The Grignard reagent must be prepared under strict anhydrous conditions (dry glassware, dry solvent). The volative solvent, diethyl ether, helps to prevent oxygen or carbon dioxide from entering the reaction vessel. Reaction of bromobenzene with magnesium in ether produces phenylmagnesium bromide. This Grignard reagent then reacts with methyl benzoate to produce the corresponding alkoxide. Reaction of the alkoxide with aqueous acid then produces the alcohol. Ethanol is often present in the technical grade of diethyl ether. If this grade rather than anhydrous were used, what effect, if any, would the ethanol have on the formation of the Grignard reagent? Explain.
In an experiment, triphenylmethanol is prepared using the Grignard reaction. The Grignard reaction involves preparation and reaction of a very nucleophilic organo-magnesium compound. The Grignard reagent is very reactive and is easily destroyed by reaction with atmospheric water, oxygen, or carbon dioxide. The Grignard reagent must be prepared under strict anhydrous conditions (dry glassware, dry solvent). The volative solvent, diethyl ether, helps to prevent oxygen or carbon dioxide from entering the reaction vessel. Reaction of bromobenzene with magnesium in ether produces phenylmagnesium bromide. This Grignard reagent then reacts with methyl benzoate to produce the corresponding alkoxide. Reaction of the alkoxide with aqueous acid then produces the alcohol.
Ethanol is often present in the technical grade of diethyl ether. If this grade rather than anhydrous were used, what effect, if any, would the ethanol have on the formation of the Grignard reagent? Explain.
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