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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: invisiblekinesis on March 14, 2011, 09:19:15 AM

Title: Salicylamide Iodination Mechanism and Equation Help
Post by: invisiblekinesis on March 14, 2011, 09:19:15 AM

I know the product will be a 1,2,4 product because of the hydroxy group directing. What I do not know is the mechanism for this or the balanced equation. We use C7H10N02 + CH3CH2OH + NaI + NaClO + Na2S2O3 + HCl but i dont know all the products. Any insight to this reaction would be greatly appreciated.

Title: Re: Salicylamide Iodination Mechanism and Equation Help
Post by: invisiblekinesis on March 14, 2011, 09:48:01 AM

im thinking the Na2S2O3 will be used to block so that I adds to the desired position. What I do not know is the intermediate molecule that contains the blocking sub. before treating with HCl.

Title: Re: Salicylamide Iodination Mechanism and Equation Help
Post by: AWK on March 14, 2011, 09:53:28 AM

Ethanol is a solvent only.

Title: Re: Salicylamide Iodination Mechanism and Equation Help
Post by: nox on March 15, 2011, 07:32:23 PM

You need an activated form of iodine, and that will have to come from two of the reagents you listed (NaI being an obvious one).

Na2S2O3 is sodium thiosulfate, which is just a mild reducing agent (think about why you'd need that).