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    (L13) - (JLD 2.0) - Reaction Mechanisms - 26th Sept

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    Mrigank Gupta
    The document discusses various reaction mechanisms including addition, substitution, and elimination reactions. It specifically describes the benzyne mechanism for nucleophilic aromatic substitution reactions where the aromatic ring is converted to a benzyne intermediate. It also discusses E1 and E2 elimination mechanisms and provides an example of an E1 elimination involving a tertiary amine oxide. Intramolecular E1 (Ei) eliminations are described including Cope and ester pyrolysis reactions.

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    (L13) - (JLD 2.0) - Reaction Mechanisms - 26th Sept

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    Mrigank Gupta
    68 views55 pages
    The document discusses various reaction mechanisms including addition, substitution, and elimination reactions. It specifically describes the benzyne mechanism for nucleophilic aromatic substitution reactions where the aromatic ring is converted to a benzyne intermediate. It also discusses E1 and E2 elimination mechanisms and provides an example of an E1 elimination involving a tertiary amine oxide. Intramolecular E1 (Ei) eliminations are described including Cope and ester pyrolysis reactions.

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    notes of reaction mechanism

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    [L13] - (JLD 2.0) - Reaction Mechanisms- 26th Sept

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    The document discusses various reaction mechanisms including addition, substitution, and elimination reactions. It specifically describes the benzyne mechanism for nucleophilic aromatic substitution reactions where the aromatic ring is converted to a benzyne intermediate. It also discusses E1 and E2 elimination mechanisms and provides an example of an E1 elimination involving a tertiary amine oxide. Intramolecular E1 (Ei) eliminations are described including Cope and ester pyrolysis reactions.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    68 views55 pages

    (L13) - (JLD 2.0) - Reaction Mechanisms - 26th Sept

    Uploaded by

    Mrigank Gupta
    The document discusses various reaction mechanisms including addition, substitution, and elimination reactions. It specifically describes the benzyne mechanism for nucleophilic aromatic substitution reactions where the aromatic ring is converted to a benzyne intermediate. It also discusses E1 and E2 elimination mechanisms and provides an example of an E1 elimination involving a tertiary amine oxide. Intramolecular E1 (Ei) eliminations are described including Cope and ester pyrolysis reactions.

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    of 55

    Reaction

    Mechanisms
    LECTURE 13 Benzyne &
    Ei Mechanism

    NaNH2

    solvent
    NH3(I)
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    Reaction
    Mechanisms
    LECTURE 13 Benzyne &
    Ei Mechanism

    NaNH2

    solvent
    NH3(I)
    Broad 3 Categories of Reactions and Mechanisms

    ADDITION

    Addition reaction occurs when two or more reactants combine to


    form a product without the loss of any atoms present in the
    reactants.

    SUBSTITUTION
    A chemical reaction during which one functional group in a
    chemical compound is replaced by another functional group.

    ELIMINATION

    An elimination reaction is a type of organic reaction in which two


    substituents are removed from a molecule.
    Type of nucleophilic substitution reaction:

    Type of nucleophilic substitution reaction:

    ● SN1
    ● SN2
    ● SNi
    ● SN2Ar
    ● SN2Th
    Type of Elimination Reactions

    There are three types of elimination reactions


    (I) E1
    (II) E2
    (III) E1cB
    Benzyne Mechanism

    Two mechanisms have been proposed for nucleophilic aromatic substitution,


    - SN2Ar
    - Benzyne mechanism
    Benzyne Mechanism
    Benzyne Mechanism

    sp2 orbitals involved in the triple bond are at 90o to the p orbitals of the aromatic pi system

    Poor overlap leads to a very weak triple bond, easily broken by a nucleophile
    Benzyne Mechanism
    Benzyne Mechanism

    NaNH2
    solvent
    NH3(I)
    Nucleophilic Substitution

    Mechanism

    Step 1
    Nucleophilic Substitution

    Mechanism

    Step 2
    Nucleophilic Substitution

    Mechanism

    Step 3
    Nucleophilic Substitution

    Na+ -NH2

    NH3, -33oC
    Example Propose mechanisms and show the expected products of the following
    reactions.

    A. 2,4-dinitrochlorobenzene + sodium methoxide (NaOCH3)


    Example Propose mechanisms and show the expected products of the following
    reactions.

    2,4-dimethylchlorobenzene + sodium hydroxide, 350 °C


    Example Propose mechanisms and show the expected products of the following
    reactions.

    p-nitrobromobenzene + methylamine (CH3— NH2)


    Example
    Nucleophilic Substitution

    ortho- meta- para-

    Never formed
    Nucleophilic Substitution

    CH3 doesn’t have effect on nucleophilic attack but electron withdrawing groups (-I) like CF3 and
    OCH3 affect the position of nucleophile
    Ei Elimination Reaction Mechanism

    ● Ei mechanism (Elimination Internal/Intramolecular) Also known as a thermal syn


    elimination or a pericyclic syn elimination

    ● Two vicinal substituents on an alkane framework leave simultaneously via a cyclic


    transition state to form an alkene in a syn elimination.
    Pyrolytic Syn Elimination Ei (Elimination Intramolecular)

    ● This type of elimination is unique because it is thermally activated and does not require
    additional reagents. This reaction mechanism is often found in pyrolysis reactions.

    ● A number of organic compounds such as an amine oxide, ester or xanthate undergo pyrolytic
    elimination of HX (in the absence of any reagent), either in an inert solvent or, in some cases,
    in the gas phase.
    Pyrolytic Syn Elimination Ei (Elimination Intramolecular)

    ● In general these eliminations follow the rate law: Rate = K [substance]


    Ei Elimination Reaction Mechanism - Cope Elimination

    When a tertiary amine oxide is heated at approximately 100oC, elimination reaction takes place as
    follows:
    Example
    Example
    Cope Elimination Regioselectivity
    Cope Elimination Regioselectivity
    Ei Elimination Reaction Mechanism - Ester Pyrolysis

    ● When subjected to temperatures above 400 °C, esters containing β-hydrogens can eliminate
    a carboxylic acid through a 6-membered transition state, resulting in an alkene.
    Example
    Example
    Example
    Ei Elimination Reaction Mechanism - Xanthate Ester Pyrolysis
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