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Sourav posted an Question
August 30, 2020 • 01:44 am 30 points
  • IIT JAM
  • Chemistry (CY)

According to me 2>3>1

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  • Suman Kumar best-answer

    i>ii>iii. This will be the order of basicity

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    ist is more basic as it is bridged and sp3 Nitrogen

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

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    3rd is least basic due to participation in resonance

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    Please ask if you don't get

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    but sir 2 is doing resonance na?

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

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

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    You must have studied bridged carbocation are highly unstable

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    1 me Nitrogen ke adjacent sp3 carbon.

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

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    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

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    by donation bridge atom will become sp2

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    Donation se sp2 kaise ?

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

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    carbocation sp2 hi hote hai

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

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

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

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

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    Happy learning

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    Priyanshu kumar Best Answer

    Sourav 1st will be more basic than 2nd and 3rd

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

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    So not easily available for donation

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

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

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

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    and btw 2 and 3 how do we check?

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    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

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