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    Chemsheets A2 1054 Acylation

    Uploaded by

    Sumaira Ali
    Acylation 1

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    © All Rights Reserved
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    Chemsheets A2 1054 Acylation

    Uploaded by

    Sumaira Ali
    472 views4 pages
    Acylation 1

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    Chemsheets a2 1054 Acylation

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    Acylation 1

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    © All Rights Reserved
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    Download as pdf or txt
    472 views4 pages

    Chemsheets A2 1054 Acylation

    Uploaded by

    Sumaira Ali
    Acylation 1

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
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    ACYLATION of ALCOHOLS / AMINES

    NUCLEOPHILIC ADDITION-ELIMINATION – acylation

    Reagent acyl chloride (RCOCl) or acid anhydride (RCOOCOR)

    Conditions

    What O
    happens
     The acyl group is R C

     Acylation is the insertion of an acyl group into a compound.


     The H on the O of an alcohol/water is replaced by an acyl group.
     The H on the N of an amine/ammonia is replaced by an acyl group.
     The other product is an acid. With amines/ammonia, this acid reacts with a second molecule
    of the amine/ammonia to form an ammonium salt of the acid.

    OVERALL a) Replace an H on the O/N to give the main product.


    +
    b) If using an amine/ammonia, the acid by-product donates H to another molecule of
    amine/ammonia

    Products Carboxylic acid (from water)


    Ester (from alcohols)
    Amide (from ammonia)
    N-substituted amide (from amines)

    Overall
    equation e.g. acylation of an alcohol (using an acyl chloride)

    O O

    R C Cl R' O H R C O R' HCl

    e.g. acylation of an amine (using an acyl chloride)

    O H O H

    R C Cl R' N H R C N R' HCl

    H H
    then +
    HCl -
    R' N H R' N H Cl

    O H O H H
    overall 2 R' + -
    R C Cl N H R C N R' R' N H Cl

    © www.CHEMSHEETS.co.uk 5-June-2016 Chemsheets A2 1054


    Example 1 e.g. ethanol + propanoyl chloride

    + HCl

    ethyl propanoate

    Example 2 e.g. methylamine + ethanoic anhydride

    -
    + 2
    N-methyl ethanamide H3N

    Example 3 e.g. water + propanoyl chloride

    Example 4 e.g. ammonia + ethanoyl chloride

    Example 5 e.g. propan-2-ol + ethanoyl chloride

    Example 6 e.g. ethylamine + propanoic anhydride

    Example 7 e.g. propylamine + butanoyl chloride

    © www.CHEMSHEETS.co.uk 5-June-2016 Chemsheets A2 1054


    Example 8 e.g. propan-1-ol + ethanoic anhydride

    Example 9 e.g. water + butanoic anhydride

    Example 10 e.g. ammonia + propanoic anhydride

    Mechanism nucleophilic addition-elimination


    for acyl
    chlorides alcohols / water amines / ammonia

    : - : -

    then
    .. ..
    H+ + RNH2 RNH3+

    Example 1 e.g. ethanol + propanoyl chloride

    : -

    nucleophilic
    addition-elimination
    ..

    Example 4 e.g. ammonia + ethanoyl chloride

    : -

    nucleophilic
    addition-elimination
    then
    .. H+ + NH3 NH4+
    NH3

    © www.CHEMSHEETS.co.uk 5-June-2016 Chemsheets A2 1054


    Example 3 e.g. water + propanoyl chloride

    Example 5 e.g. propan-2-ol + ethanoyl chloride

    Example 7 e.g. propylamine + butanoyl chloride

    © www.CHEMSHEETS.co.uk 5-June-2016 Chemsheets A2 1054

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