2013 Destroyer OC #229

[Moka11]

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Nitrobenzene is Chlorinated to yield the following intermediates:
etc etc etc.........Which intermediate resonance is the most stable


The choices all include Cl at P. Isn't NO2 a M director?

 

[Moka11]

Bump. Anyone? Am I missing something?

 

[Xo1991]

Bump. Anyone? Am I missing something?

It is an m-director, but o and p can still occur (~10% of products)

I believe what the question is getting at is how a substituent affects carbocation stability; rather than where the electrophile ends up.

 

[Moka11]

It is an m-director, but o and p can still occur (~10% of products)

I believe what the question is getting at is how a substituent affects carbocation stability; rather than where the electrophile ends up.

Ooo I thought it was 100% O/P. Thanks!