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    RXN Mechanism-4rt Part

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    AASHISH KATUWAL
    1. Elimination reactions involve the removal of atoms or groups attached to two adjacent carbon atoms, forming a multiple bond between the carbons. 2. Bimolecular elimination (E2) reactions proceed in a single step, with two molecules (the substrate and base) involved in the rate-determining step, following second-order kinetics. 3. The E2 reaction occurs through a concerted mechanism without an intermediate, and results in anti-elimination (1,2-elimination) stereochemistry.

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    RXN Mechanism-4rt Part

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    AASHISH KATUWAL
    86 views9 pages
    1. Elimination reactions involve the removal of atoms or groups attached to two adjacent carbon atoms, forming a multiple bond between the carbons. 2. Bimolecular elimination (E2) reactions proceed in a single step, with two molecules (the substrate and base) involved in the rate-determining step, following second-order kinetics. 3. The E2 reaction occurs through a concerted mechanism without an intermediate, and results in anti-elimination (1,2-elimination) stereochemistry.

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    RXn Mechanism-4rt part

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    1. Elimination reactions involve the removal of atoms or groups attached to two adjacent carbon atoms, forming a multiple bond between the carbons. 2. Bimolecular elimination (E2) reactions proceed in a single step, with two molecules (the substrate and base) involved in the rate-determining step, following second-order kinetics. 3. The E2 reaction occurs through a concerted mechanism without an intermediate, and results in anti-elimination (1,2-elimination) stereochemistry.

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    86 views9 pages

    RXN Mechanism-4rt Part

    Uploaded by

    AASHISH KATUWAL
    1. Elimination reactions involve the removal of atoms or groups attached to two adjacent carbon atoms, forming a multiple bond between the carbons. 2. Bimolecular elimination (E2) reactions proceed in a single step, with two molecules (the substrate and base) involved in the rate-determining step, following second-order kinetics. 3. The E2 reaction occurs through a concerted mechanism without an intermediate, and results in anti-elimination (1,2-elimination) stereochemistry.

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    of 9

    Comparison of SN1 and SN2 reaction

    SN1 reactions SN2 reactions


    1 Steps Multiple-steps mechanism One-step mechanism
    2 Molecularity Unimolecular, r.d.s only Bimolecular, both substrate
    involves only substrate and nucleophile are
    involved in r.d.s.
    3 Reaction kinetics first order of kinetics. second order of kinetics.

    4 Formation of It proceeds by the None


    intermediate formation of carbo-cation.
    5 Stereochemistry of the Complete inversion of
    product is racemized i.e. configuration, known as
    Stereochemistry both the retention and Walden inversion.
    inversion of configuration.
    6 Effect of substrate on Reactivity order is Reactivity order is
    rate 3o > 2o > 1o > CH3X. CH3X > 1o > 2o > 3o.
    7 Effect of solvent on Polar protic solvents like Polar aprotic solvent
    rate of rxn water favors SN1. (without OH) favors SN2
    8 Effect of nucleophile Strong or Weak Strong nucleophles of high
    on rate nucleophiles concentration

    9 Effect of base on rate Weak base and highly Weak base and highly
    polarizable group increase polarizable group increases
    the rate the rate
     Elimination reaction:
     Chemical reaction in which atoms or groups attached to two
    adjacent ( and β) carbon atoms in the substrate molecule are
    removed and multiple bond is formed.
     For example: Dehydration of ethyl alcohol.

    β α

    Ethyl alcohol Ethylene

    It involves
    • Cleavage of C-H and C-OH bond
    • Formation of C-C -bond
    During the process,
     Single bonds converts into multiple bond
     σ bonds are broken and forms of π bond.
     Saturated compound converts to unsaturated compound.
    Based on the reaction kinetics, elimination reactions are classified
    into two different types:
    • Bimolecular elimination (E2) reaction and
    • Unimolecular elimination (E1) reaction

     Bimolecular Elimination reaction (E2 rxn)


     Bimolecular: Two molecules participate in rate
    determining step (slowest step of reaction).
     Similar to the SN2 reaction.
    • Generally followed by primary alkyl halides.
    • The reaction is completed in a single step.
    • Concerted reaction mechanism (Bond breaking and
    bond formation takes place simultaneously.
    • No intermediate is formed.
     Bimolecular Elimination reaction (E2 rxn)
    Example:
    Dehydrohalogination of primary alkyl halide with
    alcoholic alkali [NaOH (caustic soda) or KOH (caustic
    potash)]
    β α β α
    -H
    R-CH2-CH2X + K-OH RCH2=CH2 + H2O + KX
    -X
    Primary alkyl alc. Alkene
    halide

    KOH (alc.) Base (B-)


    (Abstracts proton)

    β α β α
    -H
    R-CH2-CH2X + B- -X
    RCH2=CH2 + HB + X-
    substrate product Leaving
    group
    Mechanism of E2 reaction
     -hydrogen and leaving group are removed from 1st and 2nd
    carbon So known as 1,2- elimination .
     During the process, -hydrogen is removed so known as -
    elimination. B

    α
    B
    (Base)

    Substrate Leaving group


    (primary alkyl halide)
     Base started to remove a hydrogen from the -carbon to give HB.
     Electrons of C-H bond begins to move and forms C=C  double
    bond.
     Leaving group, bromide begins to depart with the bonding pair of
    electrons.
    B

    C B

    alkene
    Transition state
     Characteristics of transition state
     Partial bonds now exist between the oxygen and the -hydrogen,
    between -hydrogen and -carbon and between the -carbon and
    bromide. So Base and X, both have partial negative charge.
     The bond between -carbon–-carbon is developing double bond
    character. In order to form a pi bond; both carbons developing
    sp2 hybridization character with five bonds on carbon.
     Four atoms from the substrate (one -hydrogen, two -carbon–-
    carbon atoms and the leaving group, X) aligned in a plane. Leaving
    group is anti-periplanar (antiparallel) or trans to the β – hydrogen.
    E2 reaction mechanism
    Dehydrohalogination of primary alkyl halide with
    alcoholic alkali

    B B

    -H
    -X- B

    Substrate Product (Alkene)


    (primary alkyl halide) Transition state

    Rate determining step


    E2 reaction contd…

    R-CH2- CH2X + B- RCH2=CH2 + HB + X-


    Substrate Base product Leaving
    group
     Molecularity: As two molecules, alkyl halide and base
    participates in the rate determining step, so molecularity is
    two (2).
    The reaction is bimolecular reaction.
     Reaction kinetics:
    Rate of Reaction ∝ [RX] [B-]
    = k [RX] [B-]
    Rate of Reaction = k [substrate] [nucleophile]
    Where, k is rate constant.

    The rate depends on the concentration of both reactants


    alkyl halide and base Hence, the reaction is said to be 2nd
    order of kinetics.
    Feature of E2 reaction
     Molecularity – Bimolecular
     Kinetics – Second order of kinetics
     Steps of reaction – Single step
     Mechanism - Concerted reaction mechanism
    (A concerted reaction is a chemical reaction in which
    all bond breaking and bond making occurs in a single
    step)
     Intermediate – No
     Stereochemistry – -elimination, 1,2 elimination or
    Anti-elimination

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