How does the presence of a carbonyl group at the C2-position affect the C3-chlorination reaction of benzo[b]thiophene derivatives?

Label:chem

Topic
The C3-chlorination reaction of benzo[b]thiophene derivatives is influenced by the substituents at the C2-position.
Answer
The presence of a carbonyl group at the C2-position inhibits the C3-chlorination reaction. This is due to the formation of a hypochlorite species via hydrogen bonding with the carbonyl oxygen, preventing the formation of the hypochlorous acidium ion required for chlorination.
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