of the tosylate with a nucleophile proceeds by inversion of configuration in an SN2 process. Theproduct has the Sconfiguration.16.17Phenyl 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.16.18As shown in the text, dodecyldimethylsulfonium iodide may be prepared by reaction of dodecylmethyl sulfide with methyl iodide. An alternative method is the reaction of dodecyl iodide withdimethyl sulfide.The reaction of a sulfide with an alkyl halide is an SN2 process. The faster reaction will be the onethat uses the less sterically hindered alkyl halide. The method presented in the text will proceedfaster.16.19The molecular ion from sec-butyl ethyl ether can also fragment by cleavage of a carbon–carbonbond in its ethyl group to give an oxygen-stabilized cation of m z87.16.20All the constitutionally isomeric ethers of molecular formula C5H12O belong to one of two generalgroups: CH3OC4H9and CH3CH2OC3
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