With the aid of the table of E and C values (Table 5.5), discuss the relative basicities of 

(a) Acetone and dimethyl sulfoxide, 

(b) Dimethyl sulfide and dimethyl sulfoxide. 

Comment on a possible ambiguity for dimethyl sulfoxide.

Table 5.5.

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TABLE 5.5 Drago-Wayland parameters for some acids and bases* E Acids Antimony pentachloride Boron trifluoride lodine lodine monochloride Phenol Sulfur dioxide Trichloromethane Trimethylboron Bases Acetone Ammonia Benzene Dimethyl sulfide Dimethyl sulfoxide Methylamine p-Dioxane Pyridine Trimethylphosphine 15.1 20.2 2.05 10.4 8.86 1.88 6.18 12.6 2.02 2.78 0.57 0.70 2.76 2.66 2.23 2.39 17.2 10.5 3.31 2.05 1.70 0.90 1.65 0.32 3.48 4.67 7.08 1.21 15.26 5.83 12.00 4.87 13.10 13.40