- #1
Skyblitz
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This is a pretty basic polarity question but I'm having a hard time deciding.
I had to choose the two major products of methylbenzene with HNO3 and H2SO4.
I said that the two major products were O-methylnitrobenzene (1-methyl-2-nitrobenzene) and the other 1-methyl-4-nitrobenzene (p-methylnitrobenzene).
At anyrate, I have to chose which one would be more polar on TLC.
The more obvious choice is the 1-methyl-2-nitrobenzene which is what my friends were suggesting, however, if the methyl group is right beside the nitrobenzene, the methyl electron-donating would be negated by the nearby eletron-withdrawing nitrobenzene.
If it were the 1-methyl-4-nitrobenzene, the methyl group would make one side more electron dense, while the other side would have its electrons drawn in by the nitrobenzene group... this is where I'm confused since this means that both sides are electron-rich; therefore I'm a little stumped.
Any ideas?
Thank you.
I had to choose the two major products of methylbenzene with HNO3 and H2SO4.
I said that the two major products were O-methylnitrobenzene (1-methyl-2-nitrobenzene) and the other 1-methyl-4-nitrobenzene (p-methylnitrobenzene).
At anyrate, I have to chose which one would be more polar on TLC.
The more obvious choice is the 1-methyl-2-nitrobenzene which is what my friends were suggesting, however, if the methyl group is right beside the nitrobenzene, the methyl electron-donating would be negated by the nearby eletron-withdrawing nitrobenzene.
If it were the 1-methyl-4-nitrobenzene, the methyl group would make one side more electron dense, while the other side would have its electrons drawn in by the nitrobenzene group... this is where I'm confused since this means that both sides are electron-rich; therefore I'm a little stumped.
Any ideas?
Thank you.