zhouxiaogui
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The problem of hydrolysis of nitrile and Grignard reagent
Nitrile and Grignard reagent are hydrolyzed into ketone. I add water to hydrolyze the nitrile after the reaction, and then adjust the acid. There is
no product. Is it wrong? Can it be directly hydrolyzed with hydrochloric acid? Will there be a product?
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Amos
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This is not nearly a specific enough presentation of your problem. If you want good help, we need to know what your procedure was; all of the
chemicals involved and what times and temperatures you used. Also, how did you try to isolate a product from the reaction mixture?
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Colleen Ortiz
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Re: The problem of hydrolysis of nitrile and Grignard reagent
Grignard reagents can create an imine salt by attacking the electrophilic carbon in a nitrile. After that, the salt can be hydrolyzed to produce a
ketone.
Nitriles, R C≡N, produce ketones when they react with Grignard reagents or organolithium reagents.
The highly nucleophilic organometallic compounds contribute to the C≡N bond in the same way as aldehydes and ketones do.
The process starts with an imine salt intermediate, which is hydrolyzed to produce the ketone product.
The organometallic reagent does not have the chance to react with the ketone product since it does not develop until after the addition of water.
Aldehydes and ketones are more reactive than nitriles.
The electrophilic C in the polar nitrile group reacts with the nucleophilic C in the organometallic reagent. An intermediate imine salt complex is
formed when electrons from the CN migrate to the electronegative N.
A reaction between acids and bases. The intermediate salt protonated when aqueous acid is added, yielding the imine.
A reaction between acids and bases. Imines undergo nucleophilic addition but must be protonated to be activated (i.e. acid catalysis).
The carbonyl group of the ketone product is revealed by deprotonation.
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