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  2. Aromaticity - Wikipedia

    en.wikipedia.org/wiki/Aromaticity

    A C=C bond is shorter than a C−C bond, but benzene is perfectly hexagonal—all six carbon-carbon bonds have the same length, intermediate between that of a single and that of a double bond. A better representation is that of the circular π bond (Armstrong's inner cycle ), in which the electron density is evenly distributed through a π-bond ...

  3. Aromatic compound - Wikipedia

    en.wikipedia.org/wiki/Aromatic_compound

    Heteroarenes are aromatic compounds, where at least one methine or vinylene (-C= or -CH=CH-) group is replaced by a heteroatom: oxygen, nitrogen, or sulfur. [3] Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one ...

  4. Stereoelectronic effect - Wikipedia

    en.wikipedia.org/wiki/Stereoelectronic_effect

    The intermediate of the above reaction is the di-anion and the stereoelectronic effect that stabilizes this intermediate over the other one is the fact that the anionic charge at the para position could delocalize to the oxygen atom via orbital interaction: π(benzene) → σ*(O–CH 3).

  5. Benzene - Wikipedia

    en.wikipedia.org/wiki/Benzene

    Benzene is an organic chemical compound with the molecular formula C 6 H 6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.

  6. Simple aromatic ring - Wikipedia

    en.wikipedia.org/wiki/Simple_aromatic_ring

    Typical simple aromatic compounds are benzene, indole, and pyridine. [1] [2] Simple aromatic rings can be heterocyclic if they contain non-carbon ring atoms, for example, oxygen, nitrogen, or sulfur. They can be monocyclic as in benzene, bicyclic as in naphthalene, or polycyclic as in anthracene.

  7. Buchner ring expansion - Wikipedia

    en.wikipedia.org/wiki/Buchner_ring_expansion

    The reaction mechanism of a Buchner ring expansion begins with carbene formation from ethyl-diazoacetate generated initially through photochemical or thermal reactions with extrusion of nitrogen. carbene mechanism. The generated carbene adds to one of the double bonds of benzene to form the cyclopropane ring. carbene insertion

  8. Hückel's rule - Wikipedia

    en.wikipedia.org/wiki/Hückel's_rule

    Hückel's rule can also be applied to molecules containing other atoms such as nitrogen or oxygen. For example, pyridine (C 5 H 5 N) has a ring structure similar to benzene, except that one -CH- group is replaced by a nitrogen atom with no hydrogen. There are still six π electrons and the pyridine molecule is also aromatic and known for its ...

  9. Birch reduction - Wikipedia

    en.wikipedia.org/wiki/Birch_reduction

    The residual double bonds do not stabilize further radical additions. [2] [3] Birch reduction of benzene, also available in animated form. The reaction is known to be third order – first order in the aromatic, first order in the alkali metal, and first order in the alcohol. [4]

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