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    Wurtz Reaction

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    Anush Khillare
    The Wurtz reaction involves the coupling of two alkyl halide molecules in the presence of sodium metal in ether solvent to form a symmetrical alkane product. The reaction proceeds through an ionic mechanism where sodium forms carbanions that attack another alkyl halide molecule to form the carbon-carbon bond. Specific examples are provided of reactions forming ethane and ethylbenzene. The reaction is useful for synthesizing cyclopropane and symmetrical alkanes but produces a mixture of products if trying to form an unsymmetrical alkane.

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    Wurtz Reaction

    Uploaded by

    Anush Khillare
    173 views2 pages
    The Wurtz reaction involves the coupling of two alkyl halide molecules in the presence of sodium metal in ether solvent to form a symmetrical alkane product. The reaction proceeds through an ionic mechanism where sodium forms carbanions that attack another alkyl halide molecule to form the carbon-carbon bond. Specific examples are provided of reactions forming ethane and ethylbenzene. The reaction is useful for synthesizing cyclopropane and symmetrical alkanes but produces a mixture of products if trying to form an unsymmetrical alkane.

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    The Wurtz reaction involves the coupling of two alkyl halide molecules in the presence of sodium metal in ether solvent to form a symmetrical alkane product. The reaction proceeds through an ionic mechanism where sodium forms carbanions that attack another alkyl halide molecule to form the carbon-carbon bond. Specific examples are provided of reactions forming ethane and ethylbenzene. The reaction is useful for synthesizing cyclopropane and symmetrical alkanes but produces a mixture of products if trying to form an unsymmetrical alkane.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    173 views2 pages

    Wurtz Reaction

    Uploaded by

    Anush Khillare
    The Wurtz reaction involves the coupling of two alkyl halide molecules in the presence of sodium metal in ether solvent to form a symmetrical alkane product. The reaction proceeds through an ionic mechanism where sodium forms carbanions that attack another alkyl halide molecule to form the carbon-carbon bond. Specific examples are provided of reactions forming ethane and ethylbenzene. The reaction is useful for synthesizing cyclopropane and symmetrical alkanes but produces a mixture of products if trying to form an unsymmetrical alkane.

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    Date- 21-10-2020

    Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Ph.: 011-47623456

    REACTION OF THE DAY


    Chemistry
    Wurtz Reaction
    The coupling of alkyl halides by treatment with sodium to give a symmetrical product is called as the Wurtz
    reaction.

    Ether
    2 R – X + 2Na  R – R + 2NaX
    Alkane

    The reaction takes place in ether medium.For the same halide, the order of reactivity is pri > sec > tert and
    for the same alkyl group, it is Rl > RBr > RCI.
    Mechanism of Wurtz Reaction
    There is strong evidence in favour of ionic mechanism. Whenever sodium reacts, it becomes Na + that too
    exactly happens here.
    – +
    R – Cl + 2Na R Na + NaCl
    Carbanion in the
    form of salt

    The carbanion then attacks the second molecule of alkyl halide in S N2 fashion.

    R Na + R – Cl R – R + NaCl

    Consider some specific examples leading to formation of symmetrical alkane.

    2 Na
    2CH3 – Br CH3 – CH3
    Ether, 
    Ethane
    Na
    2C2H5 – Br C2H5 – C2H5
    Ether, 

    The coupling of alkyl and aryl halide is known an Wurtz-Fittig reaction. The main product of this reaction is
    always the cross product.

    Na
    I + CH3 – CH2 – I Ether, 
    CH2 – CH3

    Ethylbenzene

    The attempt to prepare unsymmetrical alkane by Wurtz reaction ends up with a mixture of products from
    which the seperation of components is very difficult.

    (1)
    1 2
    R – R
    1 2 Na 1 1
    R –X+R —X R –R Mixture of alkanes
    Ether,  2 2
    R –R

    Wurtz reaction is also very good at synthesis of cyclopropane.

    CH2 –I
    Na CH2
    CH2
    Et2O
    CH2 –I CH2 CH2

    

    Try Yourself
    1. On treating a mixture of two alkyl halides with sodium metal in dry ether, 2-methyl propane was obtained. The
    alkyl halides are

    (1) 2-chloropropane & chloromethane (2) 2-chloropropane & chloroethane

    (3) Chloromethane & chloroethane (4) Chloromethane & 1-chloropropane

    Answer of Question Based on Oxymercuration-Demercuration


    1. Answer (2)

    

    (2)

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