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Solubility Behavior of Organic Compounds

This document summarizes an experiment on the solubility behavior of various organic compounds. [1] Only sucrose, acetone, and ethyl alcohol were soluble in water, due to hydrogen bonding and dipole-dipole interactions between the polar solute and solvent molecules. [2] Acetone and ethyl alcohol were also soluble in ether due to London dispersion forces between the non-polar compounds. [3] The document provides chemical equations to show solute-solvent combinations formed through chemical reactions and distinguishes pairs of compounds based on their solubility behaviors and functional groups.

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Dione Gale Naval
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378 views2 pages

Solubility Behavior of Organic Compounds

This document summarizes an experiment on the solubility behavior of various organic compounds. [1] Only sucrose, acetone, and ethyl alcohol were soluble in water, due to hydrogen bonding and dipole-dipole interactions between the polar solute and solvent molecules. [2] Acetone and ethyl alcohol were also soluble in ether due to London dispersion forces between the non-polar compounds. [3] The document provides chemical equations to show solute-solvent combinations formed through chemical reactions and distinguishes pairs of compounds based on their solubility behaviors and functional groups.

Uploaded by

Dione Gale Naval
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Tumambing,Vernice Kristine M.

2010-28996

Experiment 1
Solubility Behavior of Organic Compounds

1. State what types of intermolecular forces are present in solutions formed due to intermolecular
attractions between the solute and the solvent.
Based on the results of the experiment, only three organic test compounds (sucrose, acetone and
ethyl alcohol) were soluble in water. It implies that the hydrogen bonding in the water molecules
and the dipole-dipole interactions among the polar solute molecules were replaced by hydrogen
bonding between the solute and the solvent. Of the three test compounds, the two, which are
acetone and ethyl alcohol respectively, are soluble with ether making the test compounds non-
polar since there is a non-polar compound. Ether was able to dissolve acetone and ethyl alcohol
by London Dispersion Force.
To sum it up:
Acetone-H2O London dispersion, dipole-dipole, H-bonding
Ethyl alcohol-H2O London dispersion, dipole-dipole, H-bonding
Sucrose-H2O London dispersion, dipole-dipole, H-bonding
Acetone-Ether London dispersion
Ethyl alcohol-Ether London dispersion


2. Write the balanced chemical equations for solute-solvent combinations that are formed due to
chemical reactions

Benzoic acid - NaOH
C6H5COOH(s) + OH
-
(aq) C6H5COO
-
(aq) + H2O(l)

Benzoic acid - NaHCO3
C6H5COOH(s) + HCO3
-
(aq) C6H5COO
-
(aq) + H2CO3(aq)

Phenol - NaOH
C6H5OH(aq) + OH
-
(aq) C6H5O
-
(aq) + H2O(l)

Aniline - HCl
C6H5NH2(aq) + H
+
(aq) C6H5NH3
+
(aq)

Benzyl Alcohol - H2SO4
C6H5CH2OH(aq) + 2H2SO4(aq) C6H5CH2OSO3H(s) + HSO4
-
(aq) + H3O
+
(aq)

Benzaldehyde - H2SO4
C6H5COH(aq) + 2H2SO4(aq) C6H5COSO3H(S) + HSO4
-
(aq) + H3O
+
(aq)

3. On the basis of solubility behavior, show how each of the following pairs of compounds may be
distinguished from the other.
a. CH3NH2 and CH3(CH2)5CH2NH2
CH3NH2 is a small, polar molecule and can hydrogen bond with water. CH3(CH2)5CH2NH2
can also hydrogen bond with water via the amino group but is much less polar due to the
presence of a much longer, non-polar, hydrocarbon chain.


water

soluble insoluble



b. CH3CHO and HOCH2CHO
CH3CHO is small and polar, and can hydrogen bond with water via the O on the C=O
group. It is both soluble on water and ether due to its single polar unit and a short non-polar
chain.
.
water

soluble insoluble


soluble insoluble


c. Benzylamine and benzyl alcohol
Benzylamine is soluble in 5% HCl because of its NH2 functional group while benzyl
alcohol is insoluble in 5% HCl and could be dissolved by making it react with concentrated
sulfuric acid.

water
soluble insoluble




soluble insoluble







References:
Organic Chemistry Laboratory Manual. Institute of Chemistry, UP Diliman. 2008.
http://www.wpi.edu/Academics/Depts/Chemistry/Courses/General/concept6.html#sec6-5
http://www.elmhurst.edu/~chm/vchembook/170solutions.html


insoluble soluble
water
organic compounds
+ ether + 5% NaOH
organic compounds
CH3NH2
CH3(CH2)5CH2NH2
organic compounds
+ ether
CH3CHO HOCH2CHO
organic compounds
benzyl alcohol + 5% HCl
benzylamine

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