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ORGANIC CHEMISTRY
Topic:
1. Bischler-Napieralski Reaction
2. Free Radical Mechanism
3. Aromatic Substrate Mechanism
Presented by
K. Revathi
I-M.sc. Chemistry
Bischler-Napieralski Reaction
Bischler-Napieralski
Bischler-Napieralski Mechanism
In this reaction, acyl derivatives of 𝛽-phenylethylamine
undergo cyclodehydration by reacting with phosphoryl
chloride to give dihydroisoquinoline. Subsequent
oxidation of dihydroisoquinoline with Pd on charcoal
yields corresponding isoquinolines.
Bischler-Napieralski Mechanism..
Moses Gomberg
Free Radical mechanism
In radical mechanism haemolytic bond cleavage takes place.
Initiation may happen spontaneously or may be induced by heat or
light.
The free radicals are involved in chain reaction which leads to
chain propagation.
The final step chain termination involves combination of two
radicals
Free Radical mechanism
Aromatic substrate
 The aromatic substrate is attacked by a nucleophile
with the removal of a leaving group.
 In this mechanism the strong inductive
destabilisation, few salts of ions have been isolated
and characterized.
 It has been characterized by X-ray crystallography
method.
Aromatic substrate
Aromatic substrate
Aromatic substrate reaction require
i. A good nucleophile such as one carrying oxygen, nitrogen,
or cyanide group
ii. A good leaving group such as halides
iii. Electron withdrawing substituents on the benzene ring such
as carbonyl, nitro, or cyanide groups located at ortho or
para positions to the leaving group.
•
Points to Remember
organic chemistry

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organic chemistry