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Grade: 12th pass

                        

How is -NHCOCH3 is ortho para ring activating? according to me.. the lone pair of electrons on nitrogen atom is in conjugation with the double bond of oxygen,,then howcome it is ring activating? please explain thanks :)

6 years ago

Answers : (3)

Pankaj
askIITians Faculty
131 Points
							
222-1976_Untitled.png
As you can see from the resonance structure given above, -NHCOCH3 group increases the electron density at o and p position of the ring so it is o p directing.

Thanks & Regards
Pankaj Singh
askIITians Faculty

6 years ago
ankit singh
askIITians Faculty
596 Points
							
For instance: Delocalized electron lone-pairs on the substituent can donate electron ... This activation or deactivation of the benzene ring toward electrophilic ... nitrogen, oxygen and halogen atoms form sigma-bonds to the aromatic ring exert an ... of electron withdrawal by conjugation to polar double or triple bonds, and in ...
3 months ago
Srinivasan S
27 Points
							
Dear Rajat,
 
Yes, you are correct in that there is some delocalization of lone pair of electron on NH towards C=O as happends in any amide. However, as Pankaj has mentioned, it can also donate them to the ring increasing electron density at o- & p- positions as mentioned by him.
Both effects exist in the neutral molecule.
But in the presence of an electrophile like Br2, the resonance effect comes into play and o-Bromo & p-Bromo acetanilides are formed (latter being almost a single product). 
The N-acetylation of aniline is essentially done to reduce  the o-/p- directing strength of the NH2 group. Also as a protection for NH2 (no diazotization etc. can occur), which can be removed by hydrolysis back to NH2
3 months ago
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