Amines, which coupling reaction happens?
A solution contains 1 mol each of
p-toluene diazonium chloride and p-nitrophenyl diazonium chloride. To this, 1 mol of alkaline solution of phenol is added. Predict the major product and explain your answer.14 Replies
@Dexter
Note for OP
+solved @user1 @user2... to close the thread when your doubt is solved. Mention the users who helped you solve the doubt. This will be added to their stats.so the basic medium produces a more stable phenoxide ion
...and that's about how far i've gotten
i don't think i ever learnt the mechanism for the coupling reaction, and it doesn't seem to be given in NCERT?
Coupling mechanism points
- mildly alkaline medium is better if the non-diazosalt is acidic
- mildly acidic medium is better if the non-diazosalt is basic
so mildly alkaline is better for phenol sure
but which of the two diazo salts does it pick
Yup, and mildly acidic for aniline
makes sense
Oh wait this is easier than that
There should be EWG on diazosalt
Simple as that
why?
just (-) and lack of electrons wala attraction?
Diazosalt is acting like an electrophile for EAS on phenol, so if there is EWG on diazocompound, it's a better electrophile
oh huh makes sense
got it
Mechanism of diazocoupling is just EAS on the activated benzene with electrophile as diazocompound Ar-N(+)≡N
ahh okay
yeah that clears things up thanku
+solved Opt
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