Mono-nitrated product obtained on treating meta cresol

Thread starter zorro
Start date Jan 30, 2011
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The mono-nitrated product from treating meta-cresol with HNO3 and H2SO4 can result in nitro groups being introduced at the 4 or 6 positions of the benzene ring. The discussion centers on determining which position is favored for nitration, with some suggesting 4-nitro and others 6-nitro. Factors influencing the regioselectivity include the electron-donating effects of the methyl group and steric hindrance. Ultimately, the major product is typically 4-nitro-meta-cresol due to these influences. Understanding the electrophilic aromatic substitution mechanism is crucial for predicting the outcome of such reactions.

Jan 30, 2011

zorro

Homework Statement

What is the mono-nitrated product obtained on treating meta cresol with HNO₃ and H₂SO₄?

The Attempt at a Solution

The electrophile can attack at 4 or 6 position on the benzene ring. How do I decide which one is major?

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Jan 31, 2011

chemisttree

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You say 4-nitro, I say 6-nitro... let's call the whole thing off!

Last edited: Jan 31, 2011

Jan 31, 2011

zorro

haha...ok

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