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Question

When pent-4-en-1-ol is treated with aqueous Br2/OH, the compound formed is:

A
open-chain
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B
cyclic
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C
aromatic
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D
none of these
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Solution

The correct option is B cyclic
When pent-4-en-1-ol is treated with aqueous Br2/OH.
A cyclic bromo ether is formed rather than the expected bromohydrin. In the first step, cyclic bromonium ion is formed as an intermediate which is followed by an intramolecular nucleophilic attack of hydroxide ion to obtain 2-bromotetrahydro-2H-pyran.
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