dfymarine

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an aniline reacts with an acyl chloride on the roadmap 2

to my understanding, I remember that an Nh2 is an electron-donating group that activates the benzene ring, which makes it more basic. So my answer is to add the acyl chloride to the Ortho/para position on the benzene ring.

but! it adds to the Nh2 group on the benzene ring, whyyyy?
 
Jul 29, 2009
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an aniline reacts with an acyl chloride on the roadmap 2

to my understanding, I remember that an Nh2 is an electron-donating group that activates the benzene ring, which makes it more basic. So my answer is to add the acyl chloride to the Ortho/para position on the benzene ring.

but! it adds to the Nh2 group on the benzene ring, whyyyy?
My understanding:
You wouldn't add the acyl chloride Ortho/para to the ring because for that you need AlCl3 to jump start it since I think it requires the formation of a carbocation. In this rxn, the nitrogen onthe aniline is nucleophilic and will attack the electrophilic carbon of the acyl chloride pushing the pi bond electrons to the oxygen - once this happens do a lone pair push back to the carbon and chlorine leaves because it's the a good leaving group.
 
OP
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dfymarine

10+ Year Member
5+ Year Member
Jan 3, 2007
134
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Status
Pre-Dental
My understanding:
You wouldn't add the acyl chloride Ortho/para to the ring because for that you need AlCl3 to jump start it since I think it requires the formation of a carbocation. In this rxn, the nitrogen onthe aniline is nucleophilic and will attack the electrophilic carbon of the acyl chloride pushing the pi bond electrons to the oxygen - once this happens do a lone pair push back to the carbon and chlorine leaves because it's the a good leaving group.

oh! it makes sense now! thanks!


but, if you jump start the acy chloride into a carbocation by using a lewis acid, wouldn't the Nh2 still want to attack the acyl chloride as a nucleophile?
 
Jul 11, 2009
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My understanding:
You wouldn't add the acyl chloride Ortho/para to the ring because for that you need AlCl3 to jump start it since I think it requires the formation of a carbocation. In this rxn, the nitrogen onthe aniline is nucleophilic and will attack the electrophilic carbon of the acyl chloride pushing the pi bond electrons to the oxygen - once this happens do a lone pair push back to the carbon and chlorine leaves because it's the a good leaving group.
Yup. If the arrow had FeCL3 or ALCL3 underneath it than it would have occured the way you are thinking OP.