-N(CH3) activating ortho/para director???

[sjsudentist]

In the Kaplan course:Organic chem... subject test 4 , question # 7 : States that -N(CH3) is a strongly activating ortho/para director!! However, according to my text book this would be meta directing deactivator.



Please advise !


Thanks

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[loveoforganic]

Kaplan is 100% right, your textbook is 100% wrong (assuming the group is actually -NHCH3)

 

[brightsmiles9]

I agree, NH2 is an ortho/para activator and N+ is a meta deactivator, so double check what was the substituent, NH2? or N+?

 

[fishstalker73]

...

 

[GiTsticker]

-NH-CH3 is ortho/para, electron donating, activating
-N+(CH3)3 is meta, electron withdrawing, deactivating

 

[miedvied]

-NH-CH3 is ortho/para, electron donating, activating
-N+(CH3)3 is meta, electron withdrawing, deactivating

Git has it 100% right. N-H has an electron pair to donate, and isn't very EN.
N+ obviously doesn't have an electron to donate, and will be very electron-hungry.