Question

In: Chemistry

Which substance would you expect to have the greatest solubility in a polar solvent?


Consider the two substances below.  

image.png

Which substance would you expect to have the greatest solubility in a polar solvent? Explain your reasoning based on the intermolecular forces present between molecules of the substance and molecules of the solvent.

Solutions

Expert Solution

Part I : Cis isomer

1. In cis-1,2-dichloroethene, each C—Cl bond is polar, so the overall molecule is polar.

2. Because of this, there will be dipole-dipole interactions as well as dispersion forces.

3. And intermolecular forces between the cis isomer and molecules of the solvent are greater due to greater polarity.

3. Hence Cis isomer has greater solubility in a polar solvent.

Note:

[As like dissolves in like] or [Polar substance soluble in Polar solvent]

Part II : Trans isomer

1.However, in trans-1,2-dichloroethene, the individual dipoles in the bonds cancel out, and so the molecule is non-polar.

2. In the solid state, the trans isomers can pack more closely than the cis isomers, making the intermolecular forces more effective.

3. Hence the intermolecular force between the molecules of the substance are greater in solid state.

4. And the intermolecular forces between trans isomer and molecules of the solvent are lesser due to lesser polarity.

5. Only intermolecular attractions these molecules experience are van der Waals dispersion forces.

6. Hence trans isomer has lesser solubility in polar solvent.

Conclusion:

There must be stronger intermolecular forces between the molecules of the cis isomers than between trans isomers to exhibit greater solubility in polar solvents.


Related Solutions

Why do you start with the least polar solvent/solvent mixture and progress to increasing polar solvent/solvent...
Why do you start with the least polar solvent/solvent mixture and progress to increasing polar solvent/solvent mixtures when eluting the ferrocene compounds from the column rather than starting with more polar solvent system and progressing to less polar solvents?
Which of the following is NOT a polar aprotic solvent?
Which of the following is NOT a polar aprotic solvent?  dimethylsulfoxide (DMSO) acetone DMF ethanol
What effects crystallization? What do you have to consider (solvent, temperature, solubility, etc.)? Which methods yield...
What effects crystallization? What do you have to consider (solvent, temperature, solubility, etc.)? Which methods yield a purer product, extraction or crystallization? How is crystallization different than extraction?
Q2: Which molecule would be expected to expect the highest boiling point as a pure substance...
Q2: Which molecule would be expected to expect the highest boiling point as a pure substance that are molecular isomers with the same molecular formula, C5H12? 10 vs 40 0C. - neopentane ( Hint: (CH3)4 C )
Which of the following would you expect to have a microbiome? A human An alligator A...
Which of the following would you expect to have a microbiome? A human An alligator A prion All of the above A and B Which location in a healthy animal would be least likely to have a normal microbiota? Brain Large intestine Small intestine Skin Upper respiratory tract Within a human intestine, which type of microbe would have the highest density? Archaea Bacteria Fungi Protozoa Viruses Which of the following would be considered virulence factors in bacteria? Capsule Toxin Plasmid...
Which of the following molecules would you expect to have the largest molecular dipole (which is...
Which of the following molecules would you expect to have the largest molecular dipole (which is the most polar)? a) CH4 b) CH2F2 c) CH3F d) BF3 e) CF4
in reverse phase HPLC would you expect the least polar analyte to elute first or last?...
in reverse phase HPLC would you expect the least polar analyte to elute first or last? Explain your answer.
Consider an Sn2 reaction of NaSH in a polar aprotic solvent with (CH3)2CHCH2CH2X. What would be...
Consider an Sn2 reaction of NaSH in a polar aprotic solvent with (CH3)2CHCH2CH2X. What would be the relative order of reactivity for the following X substituents? I. X= I II. X=Br III. X=Cl IV. X=F A. I>II>III>IV B.II>I>IV>III C.IV>III>II>I D.III>I>II>IV E. None of these choices
What would be the result of using a very polar solvent like methanol (instead of ethyl...
What would be the result of using a very polar solvent like methanol (instead of ethyl acetate) to develop your TLC plates?
Which one of each of the following pair of nuclides would you expect to have the...
Which one of each of the following pair of nuclides would you expect to have the longest half-life? Sr-101 or Sr-95 Co-48 or Co-53
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT