M. De Leon / Chemistry 31.

1 (2019) P a g e |1

Solubility of Organic Compounds

Matthew Rei B. De Leona, Avian Faye B. Vitalb
aNational
Institute of Molecular Biology and Biotechnology, University of the Philippines Diliman, Quezon City, Philippines
bNational
Institute of Molecular Biology and Biotechnology, University of the Philippines Diliman, Quezon City, Philippines
Performed 15 August 2019; Submitted 22 August 2019

ANSWERS TO QUESTIONS

1. Account for the solutes dissolved in the given solvent by identifying the intermolecular forces of attraction
involved.
 Hexane was not included in the table below since it is an inert compound.

Test H2O diethyl 5.0% NaOH 5.0% 5.0% HCl Conc.

Compound ether NaHCO3 H2SO4
phenol - - Ion-induced - - -
dipole, LDF
benzoic acid - - Ion-induced Ion-induced - -
dipole, LDF dipole, LDF
sucrose H-bonding, - - - - -
LDF
aniline - - - - Ion-dipole, -
H-bonding,
LDF
ethanol H-bonding, Dipole- - - - -
LDF induced
dipole, LDF
benzaldehyde - - - - - Ion-
induced
dipole, LDF

[1] Silberberg, M. In Chemistry: The Molecular Nature of Matter and Change; McGraw-Hill Companies, 2009; pp
451–456.
2. Write the balanced equations involved for solutes that dissolved with the given solvent. Draw the organic
compounds using bond-line structures.
 phenol and NaOH: C6H5OH+ NaOH→ C6H5ONa + H2O

Matthew Rei B. De Leon. Mobile: 09195075924

E-mail address: mbdeleon10@up.edu.ph
 M. De Leon / Chemistry 31.1 (2019) P a g e |2

 benzoic acid and NaOH: C6H5COOH + NaOH → C6H5COONa + H2O

 benzoic acid and NaHCO3: C6H5COOH + NaHCO3 → C6H5COONa + CO2 + H2O

 sucrose and H2O: C12H22O11 + H2O → C6H12O6 + C6H12O6

 aniline and HCl: C6H5NH2 + HCl → C6H5NH3Cl

 ethanol and H2O: C2H5OH(l) + H2O(l) → C2H5OH(aq)

 ethanol and diethyl ether: C2H5OH + (C2H5)2O → C6H16O2

Matthew Rei B. De Leon. Mobile: 09195075924

E-mail address: mbdeleon10@up.edu.ph
 M. De Leon / Chemistry 31.1 (2019) P a g e |3

 benzaldehyde and H2SO4: C7H6O + H2SO4 → C7H6O4S + H2O

[2] Lehman, J. W. Operational Organic Chemistry: A Problem-solving Approach to the Laboratory Course, 4th ed.;
Pearson Prentice Hall, 2009.
[3] Carter, J. The Effect of PH on Ethanol Preserved Muscle Tissue. Collection F 2009, 23 (1-2), 36–45.
[4] Diethyl ether ethanol. https://pubchem.ncbi.nlm.nih.gov/compound/Diethyl-ether-ethanol (accessed Aug
21, 2019).

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

[5] Fieser, L. F.; Williamson, K. L. Organic Experiments, 7th ed.; D.C. Heath, 1992; pp 574.

Matthew Rei B. De Leon. Mobile: 09195075924

E-mail address: mbdeleon10@up.edu.ph