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Dolbier HW Solutions 312 - 406 ETHERS EPOXIDES AND SULFIDES...

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of the tosylate with a nucleophile proceeds by inversion of con fi guration in an S N 2 process. The product has the S con fi guration. 16.17 Phenyl vinyl sulfoxide lacks a plane of symmetry and is chiral. Phenyl vinyl sulfone is achiral; a plane of symmetry passes through the phenyl and vinyl groups and the central sulfur atom. 16.18 As shown in the text, dodecyldimethylsulfonium iodide may be prepared by reaction of dodecyl methyl sul fi de with methyl iodide. An alternative method is the reaction of dodecyl iodide with dimethyl sul fi de. The reaction of a sul fi de with an alkyl halide is an S N 2 process. The faster reaction will be the one that uses the less sterically hindered alkyl halide. The method presented in the text will proceed faster. 16.19 The molecular ion from sec -butyl ethyl ether can also fragment by cleavage of a carbon carbon bond in its ethyl group to give an oxygen-stabilized cation of m z 87. 16.20 All the constitutionally isomeric ethers of molecular formula C 5 H 12 O belong to one of two general groups: CH 3 OC 4 H 9 and CH 3 CH 2 OC 3
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