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Chapter 17 Spring 2009
Benzene ,[object Object],[object Object],[object Object],Kekulé structure Resonance description of benzene Implication of the geometry of the structure above Shorter isolated double bonds Longer single bonds Common representation of benzene
Benzene ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
Larger aromatic hydrocarbons http://www.cem.msu.edu/~reusch/VirtualText/react3.htm
Pictures of Benzene Electrostatic  potential surface Benzene molecular orbital In top picture notice a p orbital on each C atom. Bottom picture show the overlap of the p orbitals.
Orbital picture of benzene each carbon atom is sp 2  hybridized The resonance picture indicates why each C-C bond is the same length.
Electrostatic potential surface Electron-rich portion represents  π  electron cloud
For a compound to be classified as aromatic, it must fulfill both of the of the following criteria: ,[object Object],[object Object]
Common names for aromatic compounds
IUPAC names ,[object Object],ethyl benzene ?
[object Object]
Benzyl Benzyl substituent
Disubstituted benzenes 1,2-dimethylbenzene  1,3-dimethylbenzene  1,4-dimethylbenzene IUPAC names
Same substituent meta-dichlorobenzene or, 1,3-dichlorobenzene
Different substituents These two have common root names
Different substituents These two have common root names toluene analine
Different substituents These two have common root names meta-chlorotoluene ortho-chloroanaline
Different substituents These don’t have a common root name so alphabetize the name of the substituents.
Different substituents These don’t have a common root name so alphabetize the name of the substituents. ortho-bromochlorobenzene para-bromonitrobenzene
Heat of hydrogenation data The low heat of hydrogenation means that benzene is especially stable – this extra stability is characteristic of all aromatic compounds.
Reaction of aromatic compounds ,[object Object]
What makes a compound aromatic? ,[object Object],[object Object],[object Object],[object Object]
This molecule is non-aromatic It is cyclic, completely conjugated, non-planar, and contains 8  π  electrons
This molecule is anti-aromatic Cyclic, planar, completely conjugated, and contain four  π  electrons.
Aromatic, anti-aromatic, or non-aromatic ,[object Object],[object Object],[object Object]
Aromatic compounds can have more than one ring.
Aromatic rings can contain a single ring with lots of alternating single-double bonds
atomic orbitals molecular orbitals
Anti-aromatic
The inscribed polygon method ,[object Object],[object Object],[object Object]
Label the cation, radical, and anion as aromatic, antiaromatic, or nonaromatic.
Heterocyclic aromatic compounds
 
Nucleic acids
Thymine
 
Aromatic Question Thiamin, or vitamin B1, contains a five-membered, nitrogen-sulfur heterocycle called a thiazalium ring.  Explain why the thiazolium ring is aromatic.
Cycloheptatrienyl cation, radical and anion problem
 

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Chapter17