Dimethyl sulfoxide (DMSO, Table 8.2) has a very large dipole moment (4.0 D). Using structures, show the stabilizing interactions to be expected between DMSO solvent molecules and 

(a) A dissolved sodium ion; 

(b) Dissolved water; 

(c) A dissolved chloride ion.

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TABLE 8.2 Properties of Some Common Organic Solvents (Listed in order of increasing dielectric constant) Solvent hexane 1,4-dioxane benzenet diethyl ether chloroform ethyl acetate acetic acid tetrahydrofuran dichloromethane Structure CH₂(CH₂), CH3 0 (C₂H5)₂0 CHCI 0 CH3COC₂H5 0 CH3COH CH₂Cl₂ Common abbrevation Et₂0 EtOAc HOAC THE DCM Boiling point, °C 68.7 101.3 80.1 34.6 61.2 77.1 117.9 66 39.8 Dielectric constant €* 1.9 2.2 2.3 4.3 4.8 6.0 6.1 7.6 8.9 Dipole moment 0.08 0.4 0.1 1.2 1.2 1.6 1.6 1.7 1.1 Polar Class Protic X Donor X X X X X