jyoticlub Posted August 10, 2007 Posted August 10, 2007 I am looking forward for the most plausible mechanism of the reaction between acid amide (derivative of carboxylic acid) and HNO2. although i know the general reaction ar written in my book ie. R-CONH2 + HNO2 == (HEAT) == >R-COOH + N2(evolved)+H2O mechanism would hel me identifying which kinds of acid amides and participate in such reactions.
aviridiane Posted August 11, 2007 Posted August 11, 2007 R-CONH2 + HNO2 == (HEAT) == >R-COOH + N2(evolved)+H2O Looking at the final products from the equation, I think the reaction mechanism may be somewhat similar to the reactions of primary amines with nitrous acid So if that's the case, then the mechanism would be something like this: Reagent: sodium nitrite, NaNO2 + HCl (aq) Since the diazonium salts is not stable, it decomposes readily to form nitrogen gas and a carbocation. The carbocation then reacts with water to give the carboxylic acid. Overall equation: I am not really certain, so do correct me if i am wrong.
jyoticlub Posted August 15, 2007 Author Posted August 15, 2007 thanks for your valuable effort the mechanism seems to be correct. one thing i also wanted to know if u can clear my doubt, while drawing the resonating structures of chlorobenzene how can we show partial double bond character on chlorine though it cannot expand its octet?
Fuzzwood Posted August 15, 2007 Posted August 15, 2007 It can use one of its free electron pairs, which, in turn, puts a negative charge on the entire ring.
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