After chlorosulfonation of aniline, three positions were attacked two ortho and para. How to select these attacks just in one ortho and para positions? The reaction temperature was 0 Cand then heated to 80 C
Electrophilic aromatic substitution reactions on aniline are better done by protecting -NH2 group through its conversion into -NH-CO-CH3 (i.e. by working with acetanilide rather than aniline temporarily). The new amide group is activating ortho & para directing but is less activating than the amino group.
In chlorosulfonation, the amide bulky group will direct the incoming group mostly to the para position. Of course, the amide is easily transformed back to amine by hydrolysis.
Please see the attached reference.
https://www.utdallas.edu/~scortes/ochem/OChem_Lab2/recit_notes/exp48_sulfanilamide.pdf
- Badges
- Science topic
- Similar topics
- Heat