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32 Cards in this Set

  • Front
  • Back

Epoxide:
very reactive because of ring strain

oxirane/Epoxide:
very reactive b/c of ring strain
Furan:

One lone pair in P orbital, other in spy
positive trivalent in resonance, hence less aromatic to pyrrole
furan:
aromatic w/ oxygen
group found in furosemide (diuretic)
Tetrahydrofuran
tetrahydrofuran (non-aromatic)
Pyrrole

(excessive heterocycle- lone pair delocalises in p orbital)
Aromatic
pyrrole
Pyrrolidine (non-aromatic)

Basic
pyrrolidine (non-aromatic)
Thiophene

Aromatic
thiophene
Imidazole (aromatic)

pKa = 6-7
imidazole 
pKa = 6-7
Oxazole
oxazole
Pyrazole

Aromatic
pyrazole
Triazole (3 nitrogens)
Tetrazole (4 nitrogens)
triazole (3 nitrogens)
Pyridine (aromatic)

Azomethine Nitrogen
Pi- deficient heterocycle, Lone pair in sp2 orbital, inductive stronger
pKa = 4-5
pyridine (aromatic)
pKa = 4-5
Piperidine

Basic
pKa = 9-10
piperidine
pKa = 9-10
Pyrimidine (aromatic) (1,3)
pyrimidine (aromatic) (1,3)
Piperazine (1,4)

pKa = 9-10
found in cipro derivative
piperazine (1,4)
pKa = 9-10 
found in cipro derivative
indole ("benzopyrrole")
in L-tryptophan (amino acid)
indole ("benzopyrrole")
in L-tryptophan (amino acid)
Quinoline ring
in cipro derivative
pKa = 4-5
quinoline ring
in cipro derivative 
pKa = 4-5
Isoquinoline
in Papaverine (smooth muscle relaxant)
isoquinoline
in Papaverine (smooth muscle relaxant)
Phenothiazine
in chlorpromazine (thorazine)
phenothiazine
in chlorpromazine (thorazine)
Barbiturate
not benzo-fuzed
hydantoin-like
barbiturate
not benzo-fuzed
hydantoin-like
Morpholine

Basic
Pyridazine

Aromatic
Pyrazine

Aromatic
less basic in nature than pyridine, pyridazine and pyrimidine
2H- Pyran (non aromatic)
4H-Pyran (non aromatic)
Pyrylium cation
Quinazoline
Purine
Carbazole
Pteridine
Naphthalene
Lactones

Cyclic Esters
Lactams