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    Aromaticity With Huckle's Rule

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    Sk Z
    Hückel's rule states that monocyclic planar molecules with (4n+2) π electrons are aromatic. There are four main criteria for aromaticity: 1) the molecule is cyclic, 2) fully conjugated with p orbitals at each atom, 3) planar geometry, and 4) (4n+2) π electrons. Benzene satisfies all criteria as a cyclic and planar molecule with 6 π electrons. Aromatic molecules are stabilized through delocalization of π electrons into molecular orbitals according to Hückel molecular orbital theory.

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    Aromaticity With Huckle's Rule

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    Sk Z
    81 views7 pages
    Hückel's rule states that monocyclic planar molecules with (4n+2) π electrons are aromatic. There are four main criteria for aromaticity: 1) the molecule is cyclic, 2) fully conjugated with p orbitals at each atom, 3) planar geometry, and 4) (4n+2) π electrons. Benzene satisfies all criteria as a cyclic and planar molecule with 6 π electrons. Aromatic molecules are stabilized through delocalization of π electrons into molecular orbitals according to Hückel molecular orbital theory.

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    Aromaticity, its criteria and evidence with Huckle's Rule

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    Aromaticity with Huckle's Rule

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    Hückel's rule states that monocyclic planar molecules with (4n+2) π electrons are aromatic. There are four main criteria for aromaticity: 1) the molecule is cyclic, 2) fully conjugated with p orbitals at each atom, 3) planar geometry, and 4) (4n+2) π electrons. Benzene satisfies all criteria as a cyclic and planar molecule with 6 π electrons. Aromatic molecules are stabilized through delocalization of π electrons into molecular orbitals according to Hückel molecular orbital theory.

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    81 views7 pages

    Aromaticity With Huckle's Rule

    Uploaded by

    Sk Z
    Hückel's rule states that monocyclic planar molecules with (4n+2) π electrons are aromatic. There are four main criteria for aromaticity: 1) the molecule is cyclic, 2) fully conjugated with p orbitals at each atom, 3) planar geometry, and 4) (4n+2) π electrons. Benzene satisfies all criteria as a cyclic and planar molecule with 6 π electrons. Aromatic molecules are stabilized through delocalization of π electrons into molecular orbitals according to Hückel molecular orbital theory.

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    of 7

    January 5, 2023 [BAEYERS STRAIN THEORY]

    What is Aromaticity? Also ddiscuss in detail about its


    criteria and evidence with Huckle’s Rule?
    In 1931, German chemist and physicist Sir Erich Hückel proposed a theory to help determine
    if a planar ring molecule would have aromatic properties .This is a very popular and useful rule
    to identify aromaticity in monocyclic conjugated compound. According to which a planar
    monocyclic conjugated system having ( 4n +2) delocalised (where, n = 0, 1, 2, .....) electrons are
    known as aromatic compound . For example:: Benzene, Naphthalene, Furan, Pyrole etc.
    His rule states that if a cyclic, planar molecule has 4n+2 π electrons, it is considered aromatic.
    This rule would come to be known as Hückel's Rule.

    Criteria for Aromaticity:


    1) The molecule is cyclic (a ring of atoms)
    2) The molecule is planar (all atoms in the molecule lie in the same
    same plane)
    3) The molecule is fully conjugated (p orbitals at every atom in the ring)
    4) The molecule has 4n+2 π electrons (n=0 or any positive integer).

    Why 4n+2 π Electrons?

    ♦ According to Hückel's Molecular Orbital Theory Theory,, a compound is particularly stable if all
    of its bonding molecular orbitals are filled with paired electrons.
    ♦ This is true of aromatic compounds, meaning they are quite stable.
    ♦ With aromatic compounds, 2 electrons fill the lowest energy molecular orbital, and 4
    electrons fill each
    ch subsequent energy level (the number of subsequent energy levels is denoted
    by n), leaving all bonding orbitals filled and no anti
    anti-bonding
    bonding orbitals occupied. This gives a
    total of 4n+2π electrons.
    ♦ As for example: Benzene has 66π electrons. Its first 2π electrons fill the lowest energy orbital,
    and it has 4π electrons remaining. These 4 fill in the orbitals of the succeeding energy level.
    Notice how all of its bonding orbitals are filled
    filled, but none of the anti-bonding
    bonding orbitals have any
    electrons.

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    January 5, 2023 [BAEYERS STRAIN THEORY]

    ♦ To apply the 4n+2 rule,, first count the number of π electrons in the molecule. Then, set this
    number equal to 4n+2 and solve for n. If is 0 or any positive integer (1, 2, 3,...), the rule has
    been met.
    ♦ For example, benzene has six-π
    six electrons:

    4n + 2 = π
    4n + 2 = 6
    4n + 2 = 6
    4n = 6 – 2
    4n = 4
    n = 4/4
    n=1

    For benzene,, we find that n = 1, which is a positive integer, so the rule is met.
    Molecules that have the 3 characteristics listed above (cyclic, conjugated, flat) and have this
    number of π electrons [4n +2] will be aromatic. The letter “n” is not a characteristic of the
    molecule because “n” comes from algebra, NOT from chemistry.
    chemistry

    Conditions For Aromaticity:


    Condition - 1: The Molecule Must Be Cyclic.
    Determining if a molecule is cyclic is pretty straightforward. Then, move to condition -2. If
    there’s no ring, forget it.
    Because as for example: (Z)-1,3,5
    (Z) 1,3,5 hexatriene has the same number of pi bonds (and pi
    electrons) as benzene, but isn’t aromatic. No ring, no aromaticity.
    aromaticit

    Condition*01 The Molecule Must Be Cyclic: No Exceptions


    Condition*01-

    Note By: If an Atom has 1 or more lone pair electron and is attached to an sp2 atom then this
    atom is also sp2 sp2 atom.

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    Condition - 2: Every atom in the ring must be conjugated


    conjug

    - Obviously, being cyclic isn’t a sufficient condition for aromaticity.


    “Every atom in the ring must have an available p orbital”, or
    “Every atom in the ring must be able to participate in resonance”.
    - In order for aromaticty to exist, there
    there must also be a continuous ring of pp-orbitals around the
    ring that build up into a larger cyclic “pi (π)
    ( system”.
    - Remember that the “available p orbital” condition
    condition applies not just to atoms that are part of a
    pi (π)) bond, but also atoms bearing a lone pair, a radical, or an empty p orbital (e.g.
    carbocations).
    - NOTE BY: The key thing that “kills” conjugation is a sp3 hybridized atom with four bonds
    to atoms.. Such an atom cannot participate in resonance.

    Condition - 2: Every atom in the ring must be conjugated

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    January 5, 2023 [BAEYERS STRAIN THEORY]

    Condition - 3: The Molecule Must Have [4n+2] Pi (π


    (π) Electrons
    • The third condition is that the cyclic, conjugated molecule must
    must have the correct number of pi
    (π) electrons.
    • Benzene and Cyclooctatetraene are both cyclic and conjugated, but benzene is aromatic and
    Cyclooctatetraene is not. The difference is that benzene has 6 pi (π)
    (π) electrons, and
    Cyclooctatetraene has 8 pi (π)
    (π electrons.
    • 4n+2 are not a formula which applies to see the molecule is aromatic. It is a formula that tells
    what numbers are in the magic series. If pi ((π)) electron value matches any number in this
    series then they have the capacity for aromaticity.”

    The “magic series” is: 2, 6, 10, 14, 18, 22…..


    So for n = 0 , we have [4 (0) + 2] = 2
    for n = 1 , we have [4 (1) + 2 ] = 6
    for n = 2, we have [4 (2) + 2 ] = 10
    for n = 3, we have [4 (3) +2 ] = 14
    The condition that aromatic molecules must have [4n+2] pi (π)
    ( ) electrons is sometimes called
    “Huckel’s rule”.

    Condition - 3: The Molecule Must Have [4n+2] Pi (π


    (π) Electrons

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    Condition - 4: The Molecule Must Be Flat


    - The fourth condition for aromaticity is that the molecule must be flat (planar).
    - Aromaticity
    icity is such a stabilizing property (worth 20
    20-36
    36 kcal/mol) that generally a molecule
    that is:
    o Cyclic.
    o Conjugated.
    o Has [4n+2] pi (π) electrons.
    electrons

    Condition - 4: The Molecule Must Be Flat

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    January 5, 2023 [BAEYERS STRAIN THEORY]

    NOTE BY: Annulene are monocyclic compounds containing alternating ring ring double bonds, such
    as benzene, but of different sizes. According to systematic nomenclature, Benzene is[6]
    annulene, while Cyclobutadiene is [4] annulene, whereas Cyclooctatetraene is an [8] annulene.

    Properties of Aromatic Hydrocarbons


    Hydrocarbons:
    The first compound that was categorized as an aromatic hydrocarbon was benzene”. It is also
    the most complex aryl hydrocarbon. Each carbon atom belonging to the benzene ring has two
    carbon-carbon
    carbon sigma bonds, one carbon-hydrogen
    carbon hydrogen sigma bond, and one double bond with a
    neighbouring carbon in which the pi electron is delocalized.
    • Some general properties of aromatic hydrocarbons have been listed below.
    1. These compounds exhibit aromaticity (additional stability granted by resonance)
    2. The ratio of carbon atoms to hydrogen atoms is relatively high in these types of molecules.
    3. When burnt, the aromatic hydrocarbons display a strong and sooty flame which is yellow.
    4. These compounds generally undergo electrophilic substitutions and nucleophilic aromatic
    substitution reactions.
    5. It can be noted that these compounds can be either monocyclic or polycyclic.
    6. Properties of Aromatic Hydrocarbons include that their major sources are Petroleum and coal.
    They are well known for their exceptional physical and chemical properties. Poly
    Poly-aromatic
    hydrocarbons are defined as aromatic co
    compounds
    mpounds with more than one benzene. When they
    include in atmospheric pollution then it is known as carcinogenic in nature.
    7. Hydrocarbons which have multiple bonds are unsaturated
    unsaturated in nature like alkenes and alkynes.
    They tend to give addition reactions due to this unsaturation.

    Count pi electrons in aromatic compounds


    π-bonds are simply the second bond made in a double bond. Any pure double bond is one
    sigma/σ and one pi/π π bond.
    Since any one chemical bond (meaning only one line in bond line notation) contains at most
    two electrons, count two π--electrons per double bond, and ignore the σ-electrons.
    electrons.
    If lone pairs electron present, consider the molecular geometry, and only
    only the π-electrons that
    are in the ring count towards aromaticity.

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    REFERENCE:https://www.researchgate.net/publication/329877657_Aromaticity_Antiaromaticity_Homoaromaticit
    https://www.researchgate.net/publication/329877657_Aromaticity_Antiaromaticity_Homoaromaticit
    y_and_the_Huckel_4n_2_Rule

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