In the lab for the synthesis of methyl m-nitrobenzoate from methyl benzoate using  HNO3 and  H2SO4 via EAS, the product is recrystallized to remove impurities using 95% ethanol. Would o-nitrobenzoate and methyl p-nitrobenzoate be considered impurities? If that is so, how come ethanol can remove o-nitrobenzoate and methyl p-nitrobenzoate, but has no effect on m-nitrobenzoate?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.55P
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In the lab for the synthesis of methyl m-nitrobenzoate from methyl benzoate using  HNO3 and  H2SO4 via EAS, the product is recrystallized to remove impurities using 95% ethanol. Would o-nitrobenzoate and methyl p-nitrobenzoate be considered impurities? If that is so, how come ethanol can remove o-nitrobenzoate and methyl p-nitrobenzoate, but has no effect on m-nitrobenzoate? Thank you.

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