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  • (Part 1) +Haloalkanes+and+Haloarenes

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    This document provides a summary of the SN1 unimolecular nucleophilic substitution reaction mechanism. It begins by stating that SN1 reactions are first-order reactions that depend on the concentration of the substrate. The reaction proceeds through three steps: 1) formation of a carbocation through ionization of the substrate, 2) attack of the carbocation by a nucleophile to form a protonated alcohol, and 3) deprotonation to form the alcohol product. The rate of SN1 reactions depends on factors like the stability of the carbocation intermediate, the substrate structure, the presence of pi-bonds or heteroatoms, the solvent, and the leaving group. SN1 reactions can cause partial racemization of chiral substrates

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    This document provides a summary of the SN1 unimolecular nucleophilic substitution reaction mechanism. It begins by stating that SN1 reactions are first-order reactions that depend on the concentration of the substrate. The reaction proceeds through three steps: 1) formation of a carbocation through ionization of the substrate, 2) attack of the carbocation by a nucleophile to form a protonated alcohol, and 3) deprotonation to form the alcohol product. The rate of SN1 reactions depends on factors like the stability of the carbocation intermediate, the substrate structure, the presence of pi-bonds or heteroatoms, the solvent, and the leaving group. SN1 reactions can cause partial racemization of chiral substrates

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    7 views39 pages

    (Part 1) +Haloalkanes+and+Haloarenes

    Uploaded by

    parithivasan07
    This document provides a summary of the SN1 unimolecular nucleophilic substitution reaction mechanism. It begins by stating that SN1 reactions are first-order reactions that depend on the concentration of the substrate. The reaction proceeds through three steps: 1) formation of a carbocation through ionization of the substrate, 2) attack of the carbocation by a nucleophile to form a protonated alcohol, and 3) deprotonation to form the alcohol product. The rate of SN1 reactions depends on factors like the stability of the carbocation intermediate, the substrate structure, the presence of pi-bonds or heteroatoms, the solvent, and the leaving group. SN1 reactions can cause partial racemization of chiral substrates

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    © All Rights Reserved
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    of 39

    (Part-1) Haloalkanes and

    Haloarenes
    Topic we’re going to cover today

    ● Nucleophilic Substitution Reaction: SN1


    ● Mechanism of SN1 reaction
    ● Factors affecting SN1 reaction rate
    ● Stereochemistry of SN1
    Nucleophilic Substitution Reaction

    (i) SN1 (unimolecular nucleophilic substitution)

    Those reactions in which rate of the reaction varies


    linearly with the concentration of substrate.

    r ∝ [substrate]
    r = k[substrate]

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)

    ● It is a first order reaction.

    ● It is unimolecular as well.

    ● SN1 reaction gets completed in three steps.

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)

    Step 1: Ionisation Step


    / Formation of
    Carbocation

    tert alkyl halide

    Step 2: Formation of
    protonated alcohol

    Step 3: Formation
    of alcohol (product)

    All the intermediates of the reaction is carbocation, hence


    rearrangement of carbocation is possible.
    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ?

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ? Solution

    (5 𝜶-H)

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ?

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ? Solution

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ?

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ? Solution

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ?

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ? Solution

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ?

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ? Solution

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ?

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ? Solution

    Cyclopropyl
    methyl
    carbocation

    wassimbhatt
    SN1 (unimolecular nucleophilic substitution)
    Q. What will be the product through SN1 ?

    wassimbhatt
    Factors affecting SN1 Reaction Rate
    (i) Substrate structure Rate of SN1 reaction Stability of carbocation
    Of any substrate
    ∝ formed in R.D.S

    Reactivity order

    3o > 2o > 1o > 0o

    wassimbhatt
    Factors affecting SN1 Reaction Rate
    (ii) Presence of 𝝿 - bond at ‘𝝰’ position w.r.t leaving group

    Vinyl halide

    Aryl halide

    Therefore, rate of SN1 reaction decreases.

    wassimbhatt
    Factors affecting SN1 Reaction Rate
    (iii) Presence of 𝝿 bond at ‘𝛃’ position w.r.t leaving group

    Allyl halide

    Benzyl halide

    In these compounds, rate towards SN1 is more


    because of more stability due to resonance.

    wassimbhatt
    Factors affecting SN1 Reaction Rate
    (iv) Presence of heteroatom at ‘𝝰’ position w.r.t to leaving group

    More stable
    carbocation due to
    back bonding

    wassimbhatt
    Factors affecting SN1 Reaction Rate
    (v) Presence of electron withdrawing group (EWG) in substrate

    EWG

    E.W.G decreases stability of carbocation. Hence


    rate of reaction towards SN1 decreases.

    wassimbhatt
    Factors affecting SN1 Reaction Rate
    (vi) Effect of solvent

    ● Rate of SN1 reaction ∝ Dielectric constant of solvent

    ● In general polar protic solvent like H2O, ROH etc.


    favours SN1 reaction.

    wassimbhatt
    Factors affecting SN1 Reaction Rate
    (vi) Effect of leaving group

    ● Rate of SN1 reaction ∝ leaving ability of group

    I- > Br- > Cl- F-

    wassimbhatt
    Factors affecting SN1 Reaction Rate

    Q. Arrange in the decreasing order of reactivity.

    1 2 3

    wassimbhatt
    Factors affecting SN1 Reaction Rate

    Q. Arrange in the decreasing order of reactivity.

    1 > 2 > 3

    wassimbhatt
    Factors affecting SN1 Reaction Rate

    (viii) Rate of SN1 is enhanced in the presence of Lewis acid or


    ionic salts or cation

    Rate2 > Rate1

    wassimbhatt
    Stereochemistry of SN1

    R ≠ R’ ≠ R’’

    R > R’ > R”
    (priority)

    wassimbhatt
    Stereochemistry of SN1
    x

    S R

    R S
    Enantiomers

    wassimbhatt
    Stereochemistry of SN1

    Inversion during SN1 > Retention and we get mixture of


    R and S form(Partial racemisation)

    Note:
    Racemisation ∝ Stability of carbocation
    ∝ 1/strength of nucleophile

    wassimbhatt
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