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    Chemsheets A2 1025 Reactions of Aromatics

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    xl:D c

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    Chemsheets A2 1025 Reactions of Aromatics

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    xl:D c
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    Chemsheets-A2-1025-Reactions-of-aromatics

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    51 views5 pages

    Chemsheets A2 1025 Reactions of Aromatics

    Uploaded by

    xl:D c

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 5

    REACTIONS OF AROMATICS

    Aromatic compounds are attacked by electrophiles (lone pair acceptors). This is


    because the aromatic ring is very electron rich due to the cloud of electrons above and
    ELECTROPHILIC below the ring.
    SUBSTITUTION They undergo substitution reactions where H atoms on the ring are replaced. They do
    not readily undergo addition reactions as they would lose their delocalisation and so
    extra stability in the process.

    ELECTROPHILIC SUBSTITUTION 1 – nitration

    Reagent conc HNO3 & conc H2SO4

    Conditions 50C

    What happens H atom on ring is replaced by NO2 (nitro) group

    Products Aromatic nitro compounds which are used


     to make aromatic amines (e.g. used further to make azo dyes)
     to make explosives (e.g. TNT which is 2,4,6-trinitromethybenzene)

    Overall equation

    + HNO3 + H2O

    Mechanism electrophilic substitution


    +
    Generation of electrophile = NO2 (nitronium ion)
    electrophile –
    HNO3 + 2H2SO4  NO2 + 2HSO4 + H3O
    + +

    Reaction of NO2
    electrophile - H+
    with benzene

    Example 1 e.g. methylbenzene + conc HNO3 & conc H2SO4 at 50C to make 2-nitromethylbenzene

    + HNO3 + H2O

    –
    HNO3 + 2H2SO4  NO2 + 2HSO4 + H3O
    + +

    electrophilic
    substitution NO2
    - H+

    © www.CHEMSHEETS.co.uk 30-May-2016 Chemsheets A2 1025


    Example 2 e.g. methylbenzene + conc HNO3 & conc H2SO4 at 50C to make 4-nitromethylbenzene

    Example 3 e.g. 1,3-dimethylbenzene + conc HNO3 & conc H2SO4 at 50C to make 2-nitro-1,3-dimethylbenzene

    © www.CHEMSHEETS.co.uk 30-May-2016 Chemsheets A2 1025


    ELECTROPHILIC SUBSTITUTION 2 – Friedel-Crafts acylation

    Reagent Acyl chloride or acid anhydride & AlCl3

    Conditions Anhydrous (to prevent reaction of AlCl3

    What happens H atom on ring is replaced by RCO (acyl) group

    Products Aromatic ketones – this reaction is extremely useful for adding C atoms to aromatic rings and
    any reaction that adds C atoms onto the aromatic ring is very valuable in organic synthesis.

    Overall equation

    with an acyl
    chloride + HCl

    with an acid
    anhydride

    Mechanism electrophilic substitution


    (acyl chloride) +
    electrophile = RCO (acylium ion)
    Generation of
    electrophile
    + AlCl3 + AlCl4-

    Reaction of
    electrophile
    - H+
    with benzene

    Regeneration –
    AlCl4 + H  AlCl3 + HCl
    +
    of catalyst

    Mechanism electrophilic substitution


    (acid anhydride) +
    electrophile = RCO (acylium ion)
    Generation of _ _
    electrophile
    + AlCl3 Cl3Al

    Reaction of
    electrophile
    with benzene - H+

    _
    Regeneration
    of catalyst Cl3Al + H+ AlCl3

    © www.CHEMSHEETS.co.uk 30-May-2016 Chemsheets A2 1025


    Example 4 e.g. methylbenzene with ethanoic anhydride and AlCl3 to make 2-methylphenylethanone

    + AlCl3 Cl3Al

    - H+
    electrophilic
    substitution

    Cl3Al + H+ AlCl3

    Example 5
    e.g. methylbenzene with propanoyl chloride and AlCl 3 to make

    © www.CHEMSHEETS.co.uk 30-May-2016 Chemsheets A2 1025


    Example 6
    e.g. nitrobenzene with ethanoyl chloride and AlCl3 to make

    Example 7
    e.g. 1,3-dimethylbenzene with ethanoic anhydride and AlCl3 to make

    © www.CHEMSHEETS.co.uk 30-May-2016 Chemsheets A2 1025

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