Mechanism of the reaction between iodine and propanone

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Shawaiz121
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Can anyone help me with the mechanism of the reaction between iodine and propanone ?
any site that explains all the steps in details as well .
Thanks
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mullac
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http://www.rationalskepticism.org/ch...sm-t36754.html
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MexicanKeith
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(Original post by Shawaiz121)
Can anyone help me with the mechanism of the reaction between iodine and propanone ?
any site that explains all the steps in details as well .
Thanks
The answer already given shows the Iodination you would expect under acidic conditions, the mechanism proceeding via the enol.

Under basic conditions a similar reaction occurs via the enolate, the product of such a reaction is more acidic than the starting material and hence undergoes multiple Iodination reactions. Finally the basic hydroxide ions can act as a nucleophile with loss of CI3-.

The details of the reactions of enol and enolates are explained very well in the text book 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers. The reaction I outline under basic conditions is called the Iodoform reaction, google should be able to provide you with its mechanism.
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