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Dolbier HW Solutions 319 - 1 Bromomethane CH 3 Br 1 NaBr CH...

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product is an ether. Ethers can be prepared by the Williamson ether synthesis involving an alkyl halide and an alkoxide ion. or Both the alkyl halide and the alkoxide ion are prepared from alcohols. The problem then be- comes one of preparing the appropriate alcohol (or alcohols) from the starting ester. This is readily done using lithium aluminum hydride. Then and The following sequence is also appropriate once methanol and benzyl alcohol are obtained by reduction of methyl benzoate: and Benzyl methyl ether CH 2 OCH 3 Sodium benzyloxide
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Unformatted text preview: 1 Bromomethane CH 3 Br 1 NaBr CH 3 OH Methanol Bromomethane CH 3 Br PBr 3 or HBr CH 2 OH Benzyl alcohol Sodium benzyloxide CH 2 ONa Na CH 2 Br NaOCH 3 Benzyl bromide Sodium methoxide Benzyl methyl ether CH 2 OCH 3 NaBr 1 1 CH 2 OH Benzyl alcohol Benzyl bromide CH 2 Br HBr or PBr 3 CH 3 OH Methanol Sodium methoxide CH 3 ONa Na 1. LiAlH 4 2. H 2 O COCH 3 O Methyl benzoate Benzyl alcohol Methanol CH 2 OH 1 CH 3 OH CH 2 OCH 3 CH 3 X 1 2 CH 2 O CH 2 OCH 3 CH 2 X 1 2 CH 3 O ETHERS, EPOXIDES, AND SULFIDES 413...
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