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6.1.1 Aromatic compounds GapFill

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Benzene has the molecular formula   C6H6C6H14C6H16C6H12. Its molecules are flat, hexagonal rings, which the discarded Kekulé model suggested contained alternating double and single bonds. However, it is now known that each carbon atom contributes one electron from a   2p1p3p1s orbital to form a cloud of  delocalisedunboundedgeneralisedglobalised electrons above and below the ring. This cloud is sometimes called a   δσβπ-system. The enthalpy of   hydrogenationcombustionvaporisationatomisation of benzene is less exothermic than would be expected for three separate double bonds, implying that this type of bonding makes it more stable. Molecules that experience this stabilisation are said to be '  alkalinefragrantaliphaticaromatic', while those that contain at least one benzene ring are called  atenesarenesadenesacenes.

Benzene typically undergoes electrophilic substitution reactions, such as nitration, halogenation and Friedel−Crafts reactions. The products of the latter reaction can be alkylbenzenes or  aldehydescarboxylic acidsacyl chloridesketones, depending on the reactants used.

Benzene rings in which one of the hydrogen atoms has been replaced by an OH group are called   benzolsphenylsphenolsbenzyls.

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72%