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    Functional Group Transformation Using Sn2 Reaction

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    kurniatriwijaya.2410
    The document describes the SN2 reaction mechanism and its applications. In 3 sentences: The SN2 reaction involves a nucleophilic substitution where the nucleophile attacks the substrate from the backside of the leaving group, causing inversion of configuration. SN2 reactions are stereospecific and enable the transformation of one functional group to another such as converting an alkyl halide to an alcohol, ether, or other functional groups. These reactions proceed through a single transition state involving simultaneous breaking of the old bond and formation of the new bond.

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    Functional Group Transformation Using Sn2 Reaction

    Uploaded by

    kurniatriwijaya.2410
    22 views13 pages
    The document describes the SN2 reaction mechanism and its applications. In 3 sentences: The SN2 reaction involves a nucleophilic substitution where the nucleophile attacks the substrate from the backside of the leaving group, causing inversion of configuration. SN2 reactions are stereospecific and enable the transformation of one functional group to another such as converting an alkyl halide to an alcohol, ether, or other functional groups. These reactions proceed through a single transition state involving simultaneous breaking of the old bond and formation of the new bond.

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    SN2

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    The document describes the SN2 reaction mechanism and its applications. In 3 sentences: The SN2 reaction involves a nucleophilic substitution where the nucleophile attacks the substrate from the backside of the leaving group, causing inversion of configuration. SN2 reactions are stereospecific and enable the transformation of one functional group to another such as converting an alkyl halide to an alcohol, ether, or other functional groups. These reactions proceed through a single transition state involving simultaneous breaking of the old bond and formation of the new bond.

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    © All Rights Reserved
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    Download as pptx, pdf, or txt
    22 views13 pages

    Functional Group Transformation Using Sn2 Reaction

    Uploaded by

    kurniatriwijaya.2410
    The document describes the SN2 reaction mechanism and its applications. In 3 sentences: The SN2 reaction involves a nucleophilic substitution where the nucleophile attacks the substrate from the backside of the leaving group, causing inversion of configuration. SN2 reactions are stereospecific and enable the transformation of one functional group to another such as converting an alkyl halide to an alcohol, ether, or other functional groups. These reactions proceed through a single transition state involving simultaneous breaking of the old bond and formation of the new bond.

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    of 13

    FUNCTIONAL GROUP TRANSFORMATION

    USING SN2 REACTION


    The SN2 Mechanism of
    Nucleophilic Substitution
    REACTION HO- + CH3Cl CH3OH + Cl-
    MECHANISM

    H H H H H
    -   H
    H-O: C Cl H O C Cl H O C + Cl-

    H H H

    The negative hydroxide ion Now the bond between


    brings a pair of electrons to In the transition state, the oxygen and carbon
    the partially positive carbon a bond between oxygen has formed and the chloride
    from the side with respect to and carbon is partially ion has departed. The
    the leaving group. The chlorine formed and the bond configuration of the carbon
    begins to move away with the betweencarbon and chlorine has inverted.
    pairof electrons that bonded it is partially broken. The
    to the carbon. configuration of the carbon
    atom begins to invert.
    Stereochemistry of SN2 Reactions

    Nucleophilic substitutions that exhibit


    second-order kinetic behavior are
    stereospecific and proceed with
    inversion of configuration.
    Inversion of Configuration

    nucleophile attacks carbon three-dimensional


    from side opposite bond arrangement of bonds in
    to the leaving group product is opposite to
    that of reactant
    Stereospecific Reaction
    A stereospecific reaction is one in which
    stereoisomeric starting materials give
    stereoisomeric products.
    The reaction of 2-bromooctane with
    NaOH
    (in ethanol-water) is stereospecific.
    (+)-2-Bromooctane  (–)-2-
    Octanol
    (–)-2-Bromooctane  (+)-2-
    Octanol
    • SN2 reaction are highly useful in organic
    synthesis because they enable us to convert
    one functional group in to another.
    • With the SN2 reaction, the functional group of
    a methyl, primary, or secondary alkyl halide
    can be transformed into that of an alcohol,
    ether, thiol, thioether, nitrile, ester and so on.
    OH-
    R OH Alcohol

    R'O-
    Ether
    FUNCTIONAL GROUP R OR'

    INTERCONVERSION SH- Thiol


    R SH

    R'S-
    R SR' Thioether

    CN-
    R C N Nitrile
    (-X-)
    R-X R'-C=C - R C C R' Alkyne

    R = Me, 1o, or 2o R'COO- O


    X= Cl, Br, or I R O C R' Ester

    R'3N +
    R NR3' X- Quaternary
    ammonium halide
    N3 -
    R-N3 Alkyl azide
    CH3Cl + Na OH CH3OH + NaCl

    CH3CH2OH + NaH CH3CH2O- Na+ + H-H


    Ethanol Sodium ethoxide

    + CH3I

    CH3OCH2CH3 + Na+ I-

    Ethyl methyl ether


    Exercises:
    1. Starting with (S)-2-bromobutane, outline
    syntheses of each of the following
    compounds:
    OC2H5
    a. (R) c. (R)
    O
    b. (R)
    O
    SH
    Synthesis of alkynes by elimination reaction
    • Mechanism for the E2 reaction

    O-
    O-
    CH3
    H CH3 H CH3
    H H
    C C H C C + OH
    H H Br C C
    H H Br- H H
    + Br-

    The basic ethoxide ion


    begins to remove a proton Partial bonds in the transition
    from the  karbon using its state extend from the oxygen
    electron pair to form a bond to it. atom that is removing the 
    At the same time, the electron pair hydrogen, through the carbon
    of the C-H bond begins to move skeleton of the developing
    in to become the  bond of a double double bond, to the departing
    bond, and thebromine begins to leaving group. The flow of electron
    depart with the electrons that bonded density is from the base toward
    it to the  carbon the leaving group as an electron pair
    fills the  bonding orbital of the alkene
    Synthesis of Alkynes by Elimination Reaction

    1. Dehidrohalogenation of alkyl halides

    base
    C C C C
    heat
    (-HX)
    H X

    2. Dehydration of alcohols

    acid + H2O
    C C C C
    heat
    H OH
    3. Hydrogenation of alkynes

    R R'

    H2/Ni2B C C
    syn addition H H
    (Z)-Alkene
    R C C R'
    R H
    Li or Na
    NH3or NH2 C C
    anti addition H R'
    (E)-Alkene

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