(c)Here the ether is a mixed primary–tertiary one. The best combination is the one that uses theprimary alkyl halide.The reaction between (CH3)3CBr and C6H5CH2Ois elimination, not substitution.16.816.9(b)If benzyl bromide is the only organic product from reaction of a dialkyl ether with hydrogenbromide, then both alkyl groups attached to oxygen must be benzyl.(c)Since 1 mole of a dihalide,rather than 2 moles of a monohalide, is produced per mole of ether,the ether must be cyclic.16.10As outlined in text Figure 16.4, the first step is protonation of the ether oxygen to give a dialkylox-onium ion.In the second step, nucleophilic attack of the halide ion on carbon of the oxonium ion gives4-iodo-1-butanol.The remaining two steps of the mechanism correspond to those in which an alcohol is converted to
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