Amines, which coupling reaction happens?

[outer monolith]

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.

[vale copper]

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[outer monolith]

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?

[grizzled bridge]

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

[outer monolith]

so mildly alkaline is better for phenol sure

but which of the two diazo salts does it pick

[grizzled bridge]

Yup, and mildly acidic for aniline

[outer monolith]

makes sense

[grizzled bridge]

Oh wait this is easier than that

There should be EWG on diazosalt

Simple as that

[outer monolith]

why?

just (-) and lack of electrons wala attraction?

[grizzled bridge]

Diazosalt is acting like an electrophile for EAS on phenol, so if there is EWG on diazocompound, it's a better electrophile

[outer monolith]

oh huh makes sense

got it

[grizzled bridge]

Mechanism of diazocoupling is just EAS on the activated benzene with electrophile as diazocompound Ar-N(+)≡N

[outer monolith]

ahh okay

yeah that clears things up thanku

+solved Opt