Either combination is satisfactory. The necessary reagents are prepared as shown.Isopropyl methyl ether is best prepared by the reactionThe reaction of sodium methoxide with isopropyl bromide will proceed mainly by elimination.Methyl bromide is prepared as shown previously; sodium isopropoxide can be prepared by addingsodium to isopropyl alcohol.Diethyl ether may be prepared as outlined:16.26(a)Secondary alkyl halides react with alkoxide bases by E2 elimination as the major pathway.The Williamson ether synthesis is not a useful reaction with secondary alkyl halides.(b)Sodium alkoxide acts as a nucleophile toward iodoethane to yield an alkyl ethyl ether.(R)-2-EthoxybutaneO2Na1 1 CH3CH2ICOCH2CH3CCH3CH3CH2HCH3CH3CH2H111CH3CH2CHCH3ONaSodium 2-butanolate
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