Benzene
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What is benzene ?
An aromatic compound and a cyclic compound containing three conjugated double bonds A ring of six sp2 hybrid carbon atoms each bonded to one hydrogen atom
What is the value of carbon-carbon bond length and bond angle
1.397A Angle -120
Compare the bond length of benzene, single-bond and double-bond
Carbon-carbon bond length in benzene is shorter that single-bound length, yet longer than typical double-bond length
What happens when bromine is added to benzene ?
No reaction occurs and the red bromine color remains
What reaction does benzene undergo substitution or addition?
Substitution
What is the only cyclic compound that shows resonance ?
Benzene
Define annulenes
Cyclic hydrocarbons with alternating single and double bonds
What type of bonds are present in benzene ?
3 sigma bonds
How are the hybrid orbitals arranged in benzene ?
In a trigonal planar geometry
How many pi electrons does benzene have ?
6
What are the type of molecular orbitals that the benzene has?
Three bonding orbitals → contribute to stability Three anti-bonding orbitals → higher in energy and electrons are not paired
What is the Huckel’s rule ?
What is the adverse effect of benzene?
Causes leukemia → decrease of RBC and increase in malfunctioning WBC Metabolites of benzene may react with proteins and DNA in the bone marrow alerting the production of red and white blood cells
Can people and animals make benzene nucleus ?
No, however it is a key component of the essential amino acid phenylalanine, so they must obtain phenylalanine in their diet
How do plants and bacteria get phenylalanine?
They can synthesize the aromatic ring and their own phenylalanine
Benzene derivatives have been isolated and used as what ?
Industrial reagents
Disubstituted benzenes are named using what prefixes ?(common name)
Ortho Meta Para
When is benzene called phenyl?
When the benzene ring is a substituent on another molecule
What is a benzoyl group ?
The seven-carbon unit consisting of a benzene ring and a methylene group