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Question

To synthesize the given compound via an SN2 reaction, which of the following options is appropriate:


A

5-chloro-pentan-1-ol should be treated with a base like OH

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B

5-chloro-pentan-2-ol should be treated with a base like OH

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C

5-chloro-pentan-3-ol should be treated with a base like OH

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D

None of the above

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Solution

The correct option is A

5-chloro-pentan-1-ol should be treated with a base like OH


The given compound is a cyclic ether. The base OH abstracts a proton and the resulting oxygen (anion) nucleophile displaces chloride in an intramolecular SN2:

Small amounts of the pentane-1,2-diol is also formed.


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