J. Alaba; A. Del Rosario / Chemistry 31.

1 (2019) Page | 1

Solubility of organic compounds

aDepartment of Food Science and Nutrition, University of the Philippines Diliman, Quezon City, Philippines
bDepartment of Food Science and Nutrition, University of the Philippines Diliman, Quezon City, Philippines
Performed 7 June 2019; Submitted 10 June 2019

ANSWERS TO QUESTIONS

1. Account for the solutes that dissolved in the given solvent by identifying the intermolecular
forces of attraction involved.
For acidic compounds
● Phenol dissolved in NaOH: Ion-induced, LDF
● Benzoic acid dissolved in NaOH: Ion-induced, LDF
● Benzoic acid dissolved in NaHCO3 : Ion-induced, LDF
For water-soluble compounds
● Sucrose dissolved in H2O: H bonding, LDF
● Ethanol dissolved in H2O: H bonding, LDF
● Ethanol dissolved in diethyl ether: Dipole-induced, LDF
For basic compound
● Aniline dissolved in HCl: Ion-dipole, LDF
For neutral compound
● Benzaldehyde dissolved in concentrated H2SO4: Ion-induced, LDF

2. Write the balanced equations involved for solutes that dissolved with the given solvent. Draw
the organic compounds using bond-line structures.

Acidic Comp. Balanced Equations

Phenol + NaOH C6H5OH(aq)+NaOH-(aq)→NaC6H5O-(aq) +H2CO3(aq)

Benzoic Acid + C6H5COOH(s)+ NaOH-(aq)→NaC6H5COO-(aq) H2O(l)

NaOH

Benzoic Acid + C6H5COOH(s)+ NaHCO-3(aq)→NaC6H5COO-(aq) + H2CO3(aq)

NaHCO3

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 J. Alaba; A. Del Rosario / Chemistry 31.1 (2019) Page | 2

Water-soluble Balanced Equations

Comp.

Sucrose + H2O C12H22O11(s)+ H2O(l) →C12H22O11(aq)

Ethanol + H2O C2H5OH(l) +H2O(l)→C2H5OH(aq)

Ethanol + diethyl C2H5OH(aq) +(C2H5)2O(aq) →C6H16O2(aq)

ether

Basic Comp. Balanced Equation

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 J. Alaba; A. Del Rosario / Chemistry 31.1 (2019) Page | 3

Aniline + HCl C6H5NH2(aq) + HCl(aq) →C6H5NH3(aq) + Cl-

Neutral Comp. Balanced Equation

Benzaldehyde + C7H6O(aq)+H2SO4(aq) →C7H6O4(S)+HSO4(aq)+ H3O+(aq)

concentrated
H2SO4

3. Determine the best solvent to differentiate the following pairs of compounds based on their
predicted solubility.
a. CH3NH2 and CH3(CH2)5NH2- NaOH
b. phenol and CH3(CH2)5COOH- NaHCO3
c. p-xylene and benzaldehyde- H2SO4
d. chloroform and tert-butanol- H2O
e. glucose and n-butanol- diethyl ether
REFERENCES

[1] Caserio, M.; Roberts, J.: Stewart, R. Organic Chemistry: methane to macromolecules, W. A.
Benjamin, Inc: NY, 1971.

[2] Klein, D. Student Study Guide and Solutions Manual: Organic Chemistry, John Wiley & Sons, Inc:
USA, 2015.

[3] Norris, J. The principles of organic chemistry, Mc-Graw Hill Company, Inc: NY, 1922.

[4] Organic Chemistry Help. Solubility of Organic

Molecules.http://www.chemhelper.com/solubility.html (accessed June 9, 2019).

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