For the following problems, see Table 8.2 for structures and dipole moments. Explain your reasoning in each case.

(a) With which one of the following solvents is DMSO not miscible: water, acetone, hexane, or acetonitrile?

(b) With which one of the following solvents is hexane not miscible: methanol, 1-propanol, diethyl ether, or acetone?

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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