Why doesn't Grignard Reagent undergo Nucleophilic Substitution with a Diazonium Salt? for example if we want to convert phenol to p-cresol. Then first nitrating it, then convert it to a diazonium salt and treating with a methyl grignard reagent. But the reaction dos not happen. Instead we have to use Gilmann Reagent for this process. Why?
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Phenolic group reacts with Grignard's reagent. – Mithoron Sep 24 '15 at 14:19
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@Mithoron I'm asking about a Diazonium Salt. Also a Phenol with Grignard Reagent gives us phenoxide which is not my objective. – Prachurjya Biswas Oct 04 '15 at 14:49
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1Well it's like you answered yourself - you have acidic -OH group all the time. – Mithoron Oct 04 '15 at 16:41
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ok I got it @Mithoron . You are saying that the Grignard Reagent will react with the phenolic group – Prachurjya Biswas Oct 04 '15 at 16:43
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This explains the reactivity of Grignards in more detail: http://chemistry.stackexchange.com/questions/3959/why-do-organolithium-or-grignard-reagents-act-as-nucleophiles-and-not-as-bases-w – bon May 29 '16 at 19:06