Dolbier HW Solutions 326

Dolbier HW Solutions 326 - 420 ETHERS, EPOXIDES, AND...

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16.35 Recall that p -toluenesulfonate (tosylate) is a good leaving group in nucleophilic substitution reac- tions. The nucleophile that displaces tosylate from carbon is the alkoxide ion derived from the hy- droxyl group within the molecule. The product is a cyclic ether, and the nature of the union of the two rings is that they are spirocyclic. 16.36 ( a ) Because all the peaks in the 1 H NMR spectrum of this ether are singlets, none of the protons can be vicinal to any other nonequivalent proton. The only C 5 H 12 O ether that satis f es this re- quirement is tert -butyl methyl ether. ( b ) A doublet septet pattern is characteristic of an isopropyl group. Two isomeric C 5 H 12 O ethers contain an isopropyl group: ethyl isopropyl ether and isobutyl methyl ether. The signal of the methine proton in isobutyl methyl ether will be split into more than a septet, however, because in addition to being split by two methyl groups, it is coupled to the two pro- tons in the methylene group. Thus, isobutyl methyl ether does not have the correct splitting
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