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    S 2 Reaction (Substitution Nucleophilic Bimolecular)

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    Palash Chawhan
    The document discusses the stereochemistry of SN2 and SN1 reactions. It states that SN2 reactions proceed through an inversion mechanism via a pentacoordinated transition state and result in 100% inversion of configuration. SN1 reactions are a two-step process involving carbocation formation and can potentially lead to a mixture of inversion and retention products, with more stable carbocations favoring greater racemization. Factors like solvent, leaving group, stability of carbocation intermediates, and substitution at sp2 hybridized carbons affect whether SN1 or SN2 pathways are operative.

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    S 2 Reaction (Substitution Nucleophilic Bimolecular)

    Uploaded by

    Palash Chawhan
    59 views15 pages
    The document discusses the stereochemistry of SN2 and SN1 reactions. It states that SN2 reactions proceed through an inversion mechanism via a pentacoordinated transition state and result in 100% inversion of configuration. SN1 reactions are a two-step process involving carbocation formation and can potentially lead to a mixture of inversion and retention products, with more stable carbocations favoring greater racemization. Factors like solvent, leaving group, stability of carbocation intermediates, and substitution at sp2 hybridized carbons affect whether SN1 or SN2 pathways are operative.

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    L2 (CH 1)

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    The document discusses the stereochemistry of SN2 and SN1 reactions. It states that SN2 reactions proceed through an inversion mechanism via a pentacoordinated transition state and result in 100% inversion of configuration. SN1 reactions are a two-step process involving carbocation formation and can potentially lead to a mixture of inversion and retention products, with more stable carbocations favoring greater racemization. Factors like solvent, leaving group, stability of carbocation intermediates, and substitution at sp2 hybridized carbons affect whether SN1 or SN2 pathways are operative.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    59 views15 pages

    S 2 Reaction (Substitution Nucleophilic Bimolecular)

    Uploaded by

    Palash Chawhan
    The document discusses the stereochemistry of SN2 and SN1 reactions. It states that SN2 reactions proceed through an inversion mechanism via a pentacoordinated transition state and result in 100% inversion of configuration. SN1 reactions are a two-step process involving carbocation formation and can potentially lead to a mixture of inversion and retention products, with more stable carbocations favoring greater racemization. Factors like solvent, leaving group, stability of carbocation intermediates, and substitution at sp2 hybridized carbons affect whether SN1 or SN2 pathways are operative.

    Copyright:

    © All Rights Reserved
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    Download as pdf or txt
    of 15

    SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

    6. STEREOCHEMISTRY OF SN2 REACTION

    Transition state
    (Penta-coordinated)

    Inversion of configuration
    (Walden Inversion)
    NOTE:
    SN2 reaction completes with 100% inversion of configuration.
    SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

    SN 2

    Leaving group --- wedge


    Nucleophile ---dash
    Leaving group --- dash
    Nucleophile --- wedge
    SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

    To create inversion product in Fischer


    projection replace leaving group by
    SN 2 nucleophile and exchange any one pair

    SN 2
    SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

    7. Reactivity towards SN2 reaction

    Branching at beta
    position decreases
    rate of SN2
    SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

    NOTE:
    Allyl and benzyl halide shows SN2 reaction in good amount.

    (Allyl halide) (Benzyl halide)

    shows SN2 reaction in excellent amount

    Rate towards SN2 reaction


    SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

    8. SN2 reaction does not take place in

    Vinyl halide

    Aryl halide

    Neopentyl halide
    NOTE :
    SN1 and SN2 reaction does not take place at sp2 hybridized carbon atom
    SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)

    Compare the rate towards SN2 reaction


    SN2 REACTION (SUBSTITUTION NUCLEOPHILIC BIMOLECULAR)
    SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)

    MECHANISM
    1st step :

    2nd step :
    SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)

    CHARACTERISTICS
    1. It is a two step reaction.
    2. Kinetics of reaction

    ROR  lkyl halide]

    3. Rate is independent of concentration of nucleophile.


    4. Carbocation intermediate is formed. Rearrangement may be possible.
    5. SN1 reaction is favoured by polar protic solvent (Ex. H2O, ROH )

    Helps in ionizing bond.


    Helps in stabilization of charges.
    SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)

    6. STEREOCHEMISTRY OF SN1 REACTION


    Retention product

    ENANTIOMERS
    Inversion product
    (Nu occupies a
    NOTE: position opposite to
    Theoretically , racemic mixture must be formed that of leaving
    but inversion product dominates over retention product. group)
    Partial racemization takes place.
    More the stability of carbocation, more will be racemization.

    (contact ion pair)


    SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)

    7. Reactivity towards SN1 reaction  stability of carbocation intermediate

    If leaving group is different then R-I > R-Br > R-Cl > R-F

    8. SN1 reaction does not take place in

    Bredt’s rule violation

    Vinyl halide Aryl halide


    SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)

    Compare rate towards SN1 reaction


    SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)
    SN1 REACTION (SUBSTITUTION NUCLEOPHILIC UNIMOLECULAR)

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