Shweta Thakur posted an Question
November 06, 2020 • 23:25 pm 30 points
  • IIT JAM
  • Chemistry (CY)

Why secondary and tertiary alcohol react with halogen acid by sn1 and and primary alcohol react with halogen acid by sn2

why secondary and tertiary alcohol react with halogen acid by sn1 and and primary alcohol react with alcohol by sn2

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    Priyanshu kumar Best Answer

    Secondary, tertiary, allylic, and benzylic alcohols appear to react by a mechanism that involves the formation of a carbocation in an SN1 reaction with the protonated alcohol acting as the substrate. Not all acid-catalyzed conversions of alcohols to alkyl halides proceed through the formation of carbocations. Primary alcohols and methanol react to form alkyl halides under acidic conditions by an SN2 mechanism.

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    please ask if any doubt

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    although we say that more the stability lessee will be reactivity but in case of alcohol tertiary is more stable so it should be least reactive n??

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    but in book it is given that it is more reactive

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    see this page

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    for stability we generally consider thermodynamic stability...Tertiary carbocations are stable by inductive effect and hyper conjugation, and therefore have the tendency to sustain the positive charge on the carbon atom and stay like this for long. That is why we call it stable: it can stay that way longer.

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    kinetic theory suggests that tertiary carbocation are most reactive too

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    Kinetic theory illustrates that the reactants present in the container randomly move in a container without any energy loss. Now imagine that there is a carbocation that is not so stable (take n-butane carbocation as an example) and now if a nucleophile would want to attack the cation, how could it attack it if it is not able to hold up by itself? The cation must hold on to itself in order to let the nucleophile come to it and then attack it. Tertiary carbocations have the stability to hold up like that and allow the nucleophile to attack it.

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    now got this shweta?. Differentiate this by thermodynamic stability and kinetically reactivity

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    kinetic theory ik Baar dobara bta do

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    nucleophile achhe se attack karega ...jb intermediates achhe se positive charge ko hold karega...tertiary carbocation positive charge ko achhe se hold krke rakhte hai...then kinetically reactive hote hai or order 3>2>1 rhte hai...and thermodynamically to hote hi hai...so order remain same

  • comment-profile-img>
    Dinesh khalmaniya 1 best-answer

    because in SN1 bond between C and L (leaving group) break so here in the first step intermediate carbocation forms. we know the stability of carbocation is 3>2>1 so in case of 3° always SN1 takes place. If we talk about SN2, here in rds nucleophilile attack on R-L so eare of reaction depends on reactant as well as nucleophile. bulkier rhe R-L, difficult to attack by nucleophile so in 1° RL always SN2 takes place

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    any doubt?

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    sir plz wait

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    writing

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    although we say that more the stability lessee will be reactivity but in case of alcohol tertiary is more stable so it should be least reactive n??

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    m sending u the picture

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    this

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    same order will be just like i send

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    although we say that more the stability lessee will be reactivity but in case of alcohol tertiary is more stable so it should be least reactive n??

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    plz expalin this

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    yes wait I'm bit busy

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    No, shweta here we will check the stability of intermediate, more the stability more is the formation of intermediate so more will be the rate of reaction

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    ok

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    ok intermediate to carbocation he hai n

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    sir to. carbocation to tertiary stable hai mtb least reactive

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    yes

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    yes, 3° carbocation is most stable so SN1 takes place

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    bs itna yaad rkho ki jis reaction me intermediate carbocation bnta he, vha pr rate of reaction dekhne k liye stability dekho. jitan intermediate stable hoga rate of reaction utni hi jada hogi

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    ok sir thanku

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    FIR ek ho Jo concept hai jis mein stability or reactivity inversely related hote hain vo to sahi hai n

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    yes

  • Suman Kumar

    In Sn1 carbocation is formed so 3⁰ ,2⁰ carbocation will be more stable. Primary alcohol will undergo Sn2 mechanism

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