Friedel craft rxn.

Why aniline, phenol doesn't undergo Friedel craft rxn. ,( ig they might go under vigorous conditions )unlike anisole as all exert +M
15 Replies
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Opt
Opt2mo ago
Oh this is simple. This is just because the lone pairs are better electron centres for the electrophile to attack than benzene ring.
Say_miracle_shadow
Say_miracle_shadowOP2mo ago
but why the lone pair of Anisole aren't better electron centres for the electrophile to attack than benzene ring
hardcoreisdead
hardcoreisdead2mo ago
aniline has nh2 which is a very good erg , the electron on N of nh2 directly go on the lewis acid used making nr3+ which is a very good ewg does preventing eas
Say_miracle_shadow
Say_miracle_shadowOP2mo ago
erg mtlb?
hardcoreisdead
hardcoreisdead2mo ago
edg
Opt
Opt2mo ago
Anisole can also have the electrophile attack on O, but, we need to disconnect another group from O to satisfy its valency, and both methyl and phenyl groups are worse leaving groups than whatever electrophile attacked.
hardcoreisdead
hardcoreisdead2mo ago
also phenol does show FCR but products are very less
Say_miracle_shadow
Say_miracle_shadowOP2mo ago
-H is poor/good leaving grp? wrt OH and NH2
hardcoreisdead
hardcoreisdead2mo ago
matlab?
Say_miracle_shadow
Say_miracle_shadowOP2mo ago
anisole ke case mein agar methyl aur phenyl r bad leaving grp toh phenol aur aniline ke case mein H kaise leaving grp h?
itsav23
itsav232mo ago
see the issue is alcl3 aniline and phenol dono main there is sm interaction with alcl3 which makes the catalyst less reactve. aniline main lp coordinats with alcl3 which deactivates the ring instead of making it more reactive. and for phenol, oh grp does hbonding and also interacts with alcl3. plus its already reactive enough for eas toh side rxn dominates anisole is a chill dude and och3 doesn't interfere with alcl3 toh the rxn is possible yeah this too, side rxns dominates
iTeachChem
iTeachChem2w ago
+solved @hardcoreisdead @itsav23
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