Question

Which of the following is more likely to be soluble in benzene \(\left(\mathrm{C}_{6} \mathrm{H}_{6}\right) ?\) In each case, explain your answer. (a) \(\mathrm{CCl}_{4}\) or \(\mathrm{NaCl}\) (b) hexane \(\left(\mathrm{C}_{6} \mathrm{H}_{14}\right)\) or glycerol \(\left(\mathrm{CH}_{2} \mathrm{OHCHOHCH}_{2} \mathrm{OH}\right)\) (c) acetic acid \(\left(\mathrm{CH}_{3} \mathrm{COOH}\right)\) or heptanoic acid \(\left(\mathrm{C}_{6} \mathrm{H}_{13} \mathrm{COOH}\right)\) (d) HCl or propylchloride \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\right)\)

Short answer

a) CCl4 or NaCl Answer: CCl₄ is more likely to be soluble in benzene because it is a nonpolar substance and benzene is a nonpolar solvent. b) Hexane (C6H14) or Glycerol (CH2OHCHOHCH2OH) Answer: Hexane is more likely to be soluble in benzene because it is a nonpolar substance and benzene is a nonpolar solvent. c) Acetic acid (CH3COOH) or Heptanoic acid (C6H13COOH) Answer: Heptanoic acid is more likely to be soluble in benzene due to its longer nonpolar hydrocarbon chain, making it have a higher nonpolar character compared to acetic acid. d) HCl or Propylchloride (CH3CH2CH2Cl) Answer: Propylchloride is more likely to be soluble in benzene since it's a nonpolar substance and benzene is a nonpolar solvent.

Step-by-step solution

Identify the polarity of each substance

Carbon tetrachloride (CCl₄) is a nonpolar molecule because the electronegativity difference between carbon and chlorine is small, and the shape of the molecule is symmetric. Sodium chloride (NaCl), on the other hand, is an ionic compound and hence very polar.

Determine solubility in benzene

Since benzene is a nonpolar solvent, it would more likely dissolve a nonpolar substance. Therefore, CCl₄ is more likely to be soluble in benzene compared to NaCl. #b) Hexane (C6H14) or Glycerol (CH2OHCHOHCH2OH)#

Identify the polarity of each substance

Hexane (C₆H₁₄) is a nonpolar hydrocarbon molecule. Glycerol (CH₂OHCHOHCH₂OH) is a polar molecule, as it has three hydroxyl groups that can form hydrogen bonds.

Determine solubility in benzene

Benzene, as a nonpolar solvent, will more likely dissolve hexane, the nonpolar substance. Hence, hexane is more likely to be soluble in benzene compared to glycerol. #c) Acetic acid (CH3COOH) or Heptanoic acid (C6H13COOH)#

Identify the polarity of each substance

Both acetic acid and heptanoic acid are carboxylic acids and are polar due to the presence of the polar COOH group. However, heptanoic acid has a longer nonpolar hydrocarbon chain.

Determine solubility in benzene

Heptanoic acid, with its longer nonpolar hydrocarbon chain, is likely to have a higher nonpolar character, making it more soluble in benzene compared to acetic acid. #d) HCl or Propylchloride (CH3CH2CH2Cl)#

Identify the polarity of each substance

Hydrogen chloride (HCl) is polar due to its electronegativity difference between hydrogen and chlorine atoms. Propylchloride (CH₃CH₂CH₂Cl) is a nonpolar alkyl halide because any electronegativity difference between carbon and chlorine is negated by its symmetric molecular structure.

Determine solubility in benzene

Benzene would more likely dissolve propylchloride since it's a nonpolar substance. Thus, propylchloride is more likely to be soluble in benzene compared to HCl.