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Ask iit jee aieee pet cbse icse state board community Community Discussion Question: Sn1 n Sn2 mechanism
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sonal_01 (91)

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which type of compounds undergo SN1 n SN2 mechanism??
    
punnima (563)

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SN1 reactivity: ==============================>
                      CH3- < CH3CH2-  < (CH3)2CH-  < (CH3)3C-
                            primary         secondary      tertiary
SN2 reactivity        Methyl > 1o        > 2o >>> 3o   
:                    <==============================
                   

VARSHA KRISHNAN....
------------------------------------
IIT is always a word which rises E thru' d body. But 2 achieve it U hav 2 drain out d entire E out of the body....

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ashish040191 (142)

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Sn1 is favoured when intemediate is a stable carbocation(tertiary),
Sn2 is favoured when reaction occurs through a transition state(no carbocation)
ther4 primary and secondary favours Sn2
 
 
generally, strong nucleophiles e.g OH- favors Sn2, and weak Nu e.g water  favours Sn1
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Conjurer (654)

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When concentration of base is very high and/or a very strong base is used, reaction proceeds by Sn2.

Plus the criteria written in the above posts.



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eistien (343)

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one small correction when it is a stong base elimination takes place and there is less room for substitution
 
SN2 is preferred by substrates which are less sterically hindered in their transition state (preferred when B carbonyl group is there especially)
 
SN1 is preferred by those whose carbocations are highle stable!!!
thats all!!!
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snehasharma (34)

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for SN1 mechanism, carbocation must be stable. it can be b'coz of resonance or backbonding..........
for SN2, it should be crowded

do rate me.....
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Conjurer (654)

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I was comparing between Sn1 and Sn2.A stronger base favours Sn2 than Sn1 as there is no opportunity for a carbocation to be formed.

Let us learn to dream, gentlemen, and then perhaps we shall learn the truth.
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eistien (343)

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a small correction for SN2 it shouldnt be crowded!!
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Judasrising (2)

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SN1 and SN2 are condition specific mechanisms. SN1 is a 2 step process. and SN2 is a one step process. the reason for this is, that the cpds. that undergo SN2 rxn have relatively unstable intermediates, moreover, there is no solvation of ions, hence to avoid the reverse rxn. the process is one stepped. SN1 rxn takes place when the solvent is polar-protic (i.e. it contains H+ ions and is capable of solvating ions and that for SN2 is polar- Aprotic. Also, there is a competition in Subst. and Elim. rxn. The former is favoured at lower temp. and the latter at higher temp.- Check the question for temp. conditions if given in the question)
Secondly the attacking species could be a strong/weak nucleophile. (note that when a base attacks a substrate, SN2 or E2 mech is followed) A weak base favours SN1 as its ions can easily be solvated in comparison to the stronger ones that MAY react with the solvent.
thirdly, the substrate matters. If the carbocation formed is relatively stable, then the mechanism followed is SN1, provided appropriate rxn conditions are maintained. If the cation formed is unstable, then SN2 or the respective elimination takes place.
The stability of the cation is scaled bt the nature of the grps attached to the cationic carbon. Ex: +I grps like alkyl grps will stabilise the carbocation and -I grps will destabilize it. Similarly check for Resonance factors, Hyperconjucation etc. in the correct priority order i.e. Resonance> Hyperconjugation> Inductive effect.
Hope this has helped you. Rate if satisfactory.
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sandeepramesh (1247)

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Yes read role of the solvent from morrison n boyd. Excellent description given there
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