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?

  • $\begingroup$ Phenolic group reacts with Grignard's reagent. $\endgroup$
    – Mithoron
    Commented Sep 24, 2015 at 14:19
  • $\begingroup$ @Mithoron I'm asking about a Diazonium Salt. Also a Phenol with Grignard Reagent gives us phenoxide which is not my objective. $\endgroup$ Commented Oct 4, 2015 at 14:49
  • 1
    $\begingroup$ Well it's like you answered yourself - you have acidic -OH group all the time. $\endgroup$
    – Mithoron
    Commented Oct 4, 2015 at 16:41
  • $\begingroup$ ok I got it @Mithoron . You are saying that the Grignard Reagent will react with the phenolic group $\endgroup$ Commented Oct 4, 2015 at 16:43
  • $\begingroup$ This explains the reactivity of Grignards in more detail: chemistry.stackexchange.com/questions/3959/… $\endgroup$
    – bon
    Commented May 29, 2016 at 19:06


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