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Chapter 9: Q58. (page 378)

Question: Draw a stepwise, detailed mechanism for the following intramolecular reaction that forms a cyclic ether.

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01

Step-by-Step SolutionStep 1: Formation of cyclic ethers

Cyclic ethers will be formed from intramolecular SN2 (bimolecular substitution) reactions that occur between two -OH groups

02

The mechanism of the given reaction

The conjugate acid of the -OHis the best leaving group. On reaction with an acid, the-OHbecomesO+H2, and it leaves the substrate molecule and forms a 3掳tertiarycarbocation intermediate.

Then, the other -OHacts as a nucleophile, and it forms a bond with the 3掳tertiarycarbocation, and thus, the product cyclic ether is formed.

Formation of cyclic ether

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