Nitration of Sodium Benzoate

[Toni T]

In Organic Chemistry class, we did nitration of sodium benzoate, because methyl benzoate was unavailable. Only information on methyl benzoate nitration seems to be available. Does anyone have any info on this reaction (product [ortho, para, meta, etc.), reaction mechanism, etc.)? I see only information on methyl benzoate. Thanks.

[UC]

Well, the nitrating mixture is acidic, is it not? And sodium benzoate would become what when exposed to a strong acid? With that nudge, you should be able to answer the question.

[mississippichem]

UC is right that should provide your answer. Also keep in mind though: Will there be a significant difference between the electron donating/withdrawing activities between a carboxylic acid group, methyl ester group, or a carboxylate (conjugate base) group? Also, which of these groups allows the most number of [significantly contributing] resonance forms in the non-aromatic intermediate?

[Toni T]

Thanks so much. m-nitro sodium benzoate seems the likely product. God bless you.

Edited August 3, 2010 by Toni T