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CH3CH2CH2-OH   +  Na     CH3CH2CH2-ONa

          + CH3CH2CH2-O-CH(CH3)2

(CH3)2CH-OH   +   HBr      (CH3)2CH-Br

                                         2o     alkene

The product of this attempted Williamson Synthesis using a secondary alkyl halide results not in the desired ether but in an alkene!

The alkyl halide in a Williamson Synthesis must beCH3 or 1o!

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