Question about benzene reaction

[akimhaneul]

When doing this reaction, why does it add to amine group and not to the benzene ring? Is it because it doesn't have the alcl3 that can activate the reaction?


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[averageasian]

the group youre adding is an acid acid chloride. this is not FCA. Acid chlorides can make -> anhydride, ester, amides. your starting material is an amine, thus this will result in an amide.

 

[DAT Destroyer]

View attachment 210228


When doing this reaction, why does it add to amine group and not to the benzene ring? Is it because it doesn't have the alcl3 that can activate the reaction?


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This is a very good question. First of all, it is NOT a Freidel Crafts reaction since no AlCl3 or other Lewis acid catalyst was employed. As a matter of fact, aniline is too reactive and would react with the AlCl3 and DESTROY the reaction. A Freidel Crafts reactions FAILS with electron withdrawing groups such as SO3H, CN, NO2.....and even super activators such as NH2. This reaction that I presented is a great way to protect the NH2 group when doing organic synthesis. This is a very important reaction that you may see one day in the future !!!

Hope this helps.

Dr. Romano