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14.2 Preparation of Ethers
The alcohol is deprotonated to give an alkoxide ion.
The deprotonation step can be accomplished by treating the alcohol with Na.
The reaction is subject to the restrictions of S 2 reactions since it occurs via an S 2 pathway.
The electrolyte must be a primary or methyl halide.
Secondary halides can't be used because elimination is favored over substitution.
It won't work with a tertiary halide.
N won't work.
Let's get some practice with a synthesis.
The C--O bond on the left can't be made with a Williamson ether synthesis because it requires an S 2 reaction.
The process would also work with an alkyl bromide or an alkyl chloride if we used an alkyl iodide.
How would you make each of the compounds using a synthesis ether?
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