25.1 Introducing Benzene
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Benzene chemical formula
C6H6
Characteristics of benzene
Colourless, sweet smelling, highly flammable liquid Classified as a carcinogen
Where is benzene naturally found?
In crude oil, component of petrol
Structure of benzene molecule
Hexagonal ring of 6 carbon atoms Each carbon joined to 2 other carbon atoms and 1 hydrogen atom
How is benzene classified?
As an aromatic hydrocarbon or arene
Kekulé Model
Hexagonal ring of 6 Carbon atoms Joined by alternate single and double bonds
Evidence to disprove Kekulé’s Model
Lack of reactivity of benzene Length of carbon carbon bonds in benzene Hydrogenation enthalpies
Lack of reactivity of benzene
If benzene had C=C bonds, it should decolourise bromine in an electrophilic addition reaction However: Benzene doesn’t undergo electrophilic addition reactions Benzene doesn’t decolourise bromine at room temperature and pressure
Length of Carbon-Carbon bonds in benzene
Using X ray diffraction, bond lengths in a molecule can be measured It was found that all the bonds in benzene were 0.139nm in length This is between the length of a single bond (0.153nm) and a double bond (0.134nm)