Heterocyclic Aromatic Compounds
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Define heterocyclic compounds
Aromatic compounds that have other elements present in the ring Most common →nitrogen, oxygen, and sulfur
What is pyridine?
An aromatic nitrogen analogue of benzene It has six-membered heterocyclic ring with 6 pi electrons
What is the difference between pyridine and benzene ?
Pyridine has a nitrogen instead of one of the carbons and no binding pair of electrons on nitrogen replaces the benzene’s bond to a hydrogen atom
Pyridine
What is pyrrole ?
An aromatic five-membered heterocyclic compound, with one nitrogen atom and two double bonds
What is the difference between pyrrole in pyridine ?
In pyrrole the lone pair on nitrogen occupies the p orbital and these electron take part in the pi bonding system
What is pyrimidine ?
A six-membered heterocyclic compound with two nitrogen atoms situated in a 1,3 arrangement
What is the difference between pyrimidine and pyrrole?
In pyrimidine the lone pairs are not needed for the aromatic sextet and the lone pairs are basic
Pyrrole
Pyrimidine
What is imidazole ?
An aromatic five-membered heterocyclic compound with two nitrogen atoms
What is special about imidazole?
Imidazole
What is furan ?
An aromatic five-membered heterocyclic compound with oxygen instead of one carbon
Furan
What is thiophene ?
An aromatic five-membered heterocyclic compound with sulfur atom instead of one oxygen
What is the difference between thiophene and furan ?
In thiophene the sulfur atom uses the unhybridized 3p orbital to overlap with the 2p orbitals on the carbon atoms
Thiophene