According to me 2>3>1

ist is more basic as it is bridged and sp3 Nitrogen

2nd is more basic than 3rd as its lone pair is localized here. Due to bridging N lone can't participate in delocalization.

3rd is least basic due to participation in resonance

Please ask if you don't get

but sir 2 is doing resonance na?

2 can't do resonance Sourav. Nitrogen bridging ke karan pahle hi strain me hai.

ok.. how to see btw 1 and 2..dono lone pair reso mai part nahi le rahe

You must have studied bridged carbocation are highly unstable

1 me Nitrogen ke adjacent sp3 carbon.

2 me Nitrogen ke adjacent me phenyl ring hai jo ki sp2 hybridized hai so -I effect

one more qs, if 2 and 1 are bridged how they will donate lone pair sir.. they will became unstable na.So 3 should be more stable as no bridging is present

by donation bridge atom will become sp2

Donation se sp2 kaise ?

sir agar bridge head pe +ve charge hoga.. to woh unstable nahi hoga.. only sp2 hone par unstable hoga?

carbocation sp2 hi hote hai

mai ye +ve charge ki bat kr rha sir. Ye stable hoga Bridge head pe?

Are yaar ye carbocation hai btao Sourav. Yeh to formal charge . Carbocation to Eletron deficient species hai dear

ok sir got it.. my doubt was that will all positive charge on bridge head will be unstable or not. 😊

Whatever i know should be delivered to you. That's all. 😊

Happy learning

In IInd and IIIrd lone pair on nitrogen participate in resonance with phenyl ring

So not easily available for donation

but sir after i do protonation, 2 and 3 will be more stable than 1 due to resonance

first we check availability of lone pair for donation...

by practising diff questions you can able to differentiate where you check this by protonation or by availability of lone pair

and btw 2 and 3 how do we check?

as these are nearly same type of compound so little diff between pkb values...but when you draw their resonating structure...you get some idea

in 3 that line is not there

ok