Heterocycles - ANS cyclic organic molecule where one or more carbon atoms are replaced by
heteroatoms
Heteroatoms - ANS Atoms in an organic compound other than carbon and hydrogen
Ex: Oxygen, Nitrogen, Sulfur
Two main subgroups of heterocycles - ANS 1. aromatic
2. aliphatic (non-aromatic)
Pyridine - ANS analogue of benzene where one C is replaced by N
geometry of pyridine - ANS flat/ planar geometry with 120 degree bond angles
atomic structure of pyridine - ANS sp2 hybridized atoms, 6 P electrons just like benzene
resonance structure of pyridine - ANS
Why does pyridine undergo substitution rather than addition? - ANS addition would destroy the
aromaticity
solubility of pyridine - ANS soluble in most organic solvents and completely soluble in water
why is pyridine soluble in water? - ANS -ability of pyridine to accept hydrogen bonding
interactions from water molecules d/t the lone pair of electrons on the nitrogen.
- electronegative N creates a relatively strong dipole moment in the pyridine, thus making it an
apolar compound overall.
BP of pyridine vs benzene? why? - ANS -pyridine has a higher BP than benzene even though
they have a similar weight
-why? dipole/dipole forces
Is pyridine an acid or base? - ANS weak base
will form pyridinium salt when reacted with strong acids
Two main reaction types of pyridine? - ANS 1. EAS- Electrophilic Aromatic Substitution
2. NAS- Nucleophilic Aromatic Substitution
What happens in the EAS of pyridine? - ANS a hydrogen is replaced by an electrophile
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