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Dolbier HW Solutions 309 - 403 ETHERS EPOXIDES AND...

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( c ) Here the ether is a mixed primary tertiary one. The best combination is the one that uses the primary alkyl halide. The reaction between (CH 3 ) 3 CBr and C 6 H 5 CH 2 O is elimination, not substitution. 16.8 16.9 ( b ) If benzyl bromide is the only organic product from reaction of a dialkyl ether with hydrogen bromide, 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. 16.10 As outlined in text Figure 16.4, the fi rst 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 gives 4-iodo-1-butanol. The remaining two steps of the mechanism correspond to those in which an alcohol is converted to
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