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Question

2,2-dimethyloxirane can be cleaved by :

A
acid
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B
water
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C
bromine
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D
none of the above
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Solution

The correct option is A acid
Cyclic ether can be cleaved in acidic as well as basic medium. In basic medium, nucleophilic attack occurs from less hindered site that means cleavage between C and O occurs from less hindered site.
In acidic medium, nucleophilic attack occurs from more hindered site that means cleavage between C and O occurs from more hindered site. Hence, the correct answer is option (a).

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