Rank the following compounds in order of increasing reactivity (least reactive first) in an SN1 solvolysis reaction in aqueous acetone. Explain your answers. (The structure of tert-cumyl chloride is shown in Table 17.2.)
(1) m-nitro-terfrcumyl chloride
(2) p-methoxy-terfrcumyl chloride
(3) p-fluoro-terr-cumyl chloride
(4) p-nitro-terfrcumyl chloride
Table 17.2

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TABLE 17.2 Comparison of S 1 Solvolysis Rates of Benzylic and Nonbenzylic Alkyl Halides Comparison of SN1 Solvolysis Rates of Benzylic and Nonbenzylic Alkyl Halides R-Cl + H2O 25°C 90% aqueous acetone R-OH + HCl Relative rate Alkyl chloride R-CI (CHCC Ph-CH-C Common name tert-butyl chloride o-phenethyl chloride 1.0 CH3 CH Ph-C-I tert-cumyl chloride 620 CH3 Ph,CH CI Ph,C-C benzhydryl chloride 200 trityl chloride >600,000 n 80% aqueous ethanol.