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Topic: Determining nucleophilicity upon mixing H2O & CH3CN  (Read 8166 times)

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Offline jkulier

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Determining nucleophilicity upon mixing H2O & CH3CN
« on: July 20, 2009, 10:47:57 PM »
Hi there,

in order to determine the type of reaction that occurs, I have to figure out whether or not mixing H2O and CH3CN would produce a good or poor nucleophile.

I have considered H2O giving up a proton to CH3CN, but that would not make much sense because there is no place for the proton to attach to. The other option is for CH3CN to lose a proton to water, but the same problem arises.

Any guidance would be great, because I am very lost.
Thanks in advance  :)

Offline UG

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Re: Determining nucleophilicity upon mixing H2O & CH3CN
« Reply #1 on: July 21, 2009, 05:39:57 AM »
I think that the nitrile carbon will undergo attack by water to give an sp2-hybridised intermediate imine anion. Someone please correct me if I'm wrong  ::).

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By the way, isn't the product ethanoic acid?

Offline Heory

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Re: Determining nucleophilicity upon mixing H2O & CH3CN
« Reply #2 on: July 22, 2009, 02:51:17 AM »
H2O doesn't react with MeCN at all, so neither a good nor a poor new nucleophile would be obtained by mixing the two materials.
the O of H2O is not nucleophilic enough to attack the C of MeCN unless the MeCN's N atom is protonated by which the electrophilicity of the MeCN is enhanced.

Offline orgopete

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Re: Determining nucleophilicity upon mixing H2O & CH3CN
« Reply #3 on: July 24, 2009, 09:50:46 AM »
I don't think the answer is found in the interaction of the two solvents. I think you should determine what effect pure acetonitrile and water has on the reaction. Acetonitrile is a classic dipolar aprotic solvent and improves nucleophilicity in some reactions. Water also effects a reaction. I think the answer is to compare whether a nucleophile is enhanced in acetonitrile or water and what effect water will on the overall reaction.

By the wording of the question ("type of reaction"), it would appear that a broader answer than nucleophilicity might be being sought. 
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