Destroyer OChem Question

[santal907]

I am studying the ochem section of DAT Destroyer.
The answer to the question #13 is different from Kaplan.
The question is "which group will deactivate benzene toward reaction with electrophiles?" The answer is N(+)R3. And the answer key also lists N(+)R2 for meta-directing subs. However, Kaplan lists NR2 as ortho/para-directing sub. Which one is right? Did I misunderstand something?

thanks!

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[sacjumpman]

I am studying the ochem section of DAT Destroyer.
The answer to the question #13 is different from Kaplan.
The question is "which group will deactivate benzene toward reaction with electrophiles?" The answer is N(+)R3. And the answer key also lists N(+)R2 for meta-directing subs. However, Kaplan lists NR2 as ortho/para-directing sub. Which one is right? Did I misunderstand something?

thanks!

If the Nitrogen has a lone pair on it, it will be o/p directing and activating. Thus NR2 will have a lone pair and no H is attached to the Nitrogen.

If it has no lone pairs on it and therefore has a positive formal charge, then it will be meta directing deactivating. Such as +NR2

Does that clear it up?

 

[santal907]

Yes! Thank you so much!