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?

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 synthesis of methyl m-nitrobenzoate from methyl benzoate using HNO3 and H2SO4 via EAS the product is washed with ethanol to remove impurities. By impurities do they mean o-nitrobenzoate and methyl p-nitrobenzoate? How come ethanol can remove o-nitrobenzoate and methyl p-nitrobenzoate, but has no effect on m-nitrobenzoate? Thank you.
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