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Question

Choose the appropriate reagents for the synthesis of t-butyl ethyl ether:

A

(CH3)3C-OH & C2H5-Br

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B

(CH3)3C-Br & C2H5-ONa

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C
(CH3)3C-ONa & C2H5-Br
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D
None of the above
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Solution

The correct option is C (CH3)3C-ONa & C2H5-Br

Ethers can be synthesised using sodium alkoxide and primary alkyl halides, known as Williamson ether synthesis. The mechanism involves SN2 attack of the alkoxide ion on a primary alkyl halide. When secondary or tertiary alkyl halides are used, elimination competes over substitution and an alkene will be obtained as the final product.


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