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Introduction
Solubility of a substance is defined by the maximum quantity of solute that can be dissolved in a
solvent at a certain temperature. A mixture of a solute and solvent is called a solution. Soluble and
insoluble are the terms used for the solubility of a solid with a liquid. But when it comes to the solubility of
both liquid compounds, the terms used are miscible and immiscible. Substances that can be dissolved
100% are called soluble or miscible and those that cannot be dissolved 100% are called insoluble or
immiscible. There are some factors that affect the solubility of a substance, namely, forces between
particles, pressure, and temperature. Compounds that have similar properties are mostly soluble in each
other and compounds that have different properties are mostly insoluble in each other. The rule of like
dissolves like is being applied. One example is polar to polar compounds and non-polar to non-polar
compounds.
At the molecular level, solubility is controlled by the energy balance of intermolecular forces
between solute-solute, solvent-solvent and solute-solvent molecules. Based on the solubility of a solute,
the possible results are, if the solution has less solute than the maximum amount that it is able to
dissolve, it is a dilute solution; if the amount of solute is exactly the same amount as its solubility, it is
saturated, and if there is more solute than is able to be dissolved, the excess solutes separates from the
solution.
Knowing the solubility of compounds is important because the solvent choice can determine the
possible yield of the reaction. It can also be used in looking at the relationships between solubility
properties of an organic molecule and its structure. By knowing the structure of a molecule, its function
can be predicted, such as its solubility, acidity, or basicity, stability, reactivity, etc.
This experiment aims to know the solubility of the compounds, hexane, benzamide, acetone,
ethyl alcohol, benzyl alcohol, aniline, toluene, sucrose, benzaldehyde, benzoic acid, and phenol. It also
aims to classify each compound into water soluble, ether-soluble, strong acid, weak acid, base, neutral,
miscellaneous neutral, or inert. Determination of their intermolecular forces of attraction and the chemical
reactions involved are also included.
Water
Ether
+
+
n/a
n/a
n/a
5%
NaOH
n/a
n/a
n/a
+
+
-
5%
NaHCO3
n/a
n/a
n/a
+
n/a
5%
HCl
n/a
n/a
n/a
n/a
n/a
+
Concentrated
H2SO4
n/a
n/a
n/a
n/a
n/a
n/a
Classification
of solute
S1
S1
S2
A1
A2
B
Acetone
Ethyl alcohol
Sucrose
Benzoic acid
Phenol
Aniline
+
+
+
-
Benzaldehyd
e
Benzy
alcohol
Hexane
Toluene
n/a
n/a
++
n/a
n/a
++
n/a
n/a
n/a
n/a
I
I
The main functional group in acetone or propanone is ketone with the structure RC(=O)R'. These
compounds contain a carbon-oxygen double bond known as a carbonyl group. On the other hand, ethyl
alcohol or ethanol is an alcohol in which the hydroxyl functional group (OH) is bound to a saturated
carbon atom. Sucrose contains both hydroxyl and ether groups in its structure. An ether contains an
oxygen atom bonded to two alkyl or aryl group and is of the general formula ROR'.
Compounds containing carbonyl or hydroxyl groups are considered polar due to the presence of
an electronegative atom in their structure, meaning they have a slightly positive side and a slightly
negative side. As a rule of thumb, like dissolves like. Water is a polar molecule thus it can dissolve polar
compounds. These compounds simply dissolve in water rather than reacting with it. A special type of
dipole-dipole force known as Hydrogen bonding exists between the solutes used and the water solvent.
One of the slightly positive hydrogen atoms in the water molecule is sufficiently attracted to one of the
partially negative-charged Oxygen atom of the solute. However, unlike in alcohols, ketones dont have
any hydrogen atoms attached directly to the oxygen, and so they do not form hydrogen bond with each
other.
Moreover not all groups with carbonyl or hydroxyl groups are soluble in water. Take for example,
benzoic acid and benzyl alcohol. Compounds must be of low molar mass and it should contain no more
than four to five carbon atoms, unless it is polyfunctional. For monofunctional organic compounds, the
borderline for water solubility is five Carbon atoms. This means that compounds having five Carbon
atoms may or may not be soluble in water and compounds that exceed five Carbon atoms is insoluble in
water.
Figure 4. Chemical reaction for the addition of Benzoic acid to Sodium Hydroxide yielding Sodium benzoate and water
The acidic portion of benzoic acid is the carboxyl group. Carboxylic acids exist primarily in their ionic,
conjugate base form when subjected in an adequate basic environment
Phenol reacts with sodium hydroxide solution to give a colourless solution containing sodium phenoxide:
Figure 5. Chemical reaction of Phenol with Sodium hydroxide yielding Sodium phenoxide and water.
In this reaction, the hydrogen ion has been removed by the strongly basic hydroxide ion in the sodium
hydroxide solution.
Ion-dipole forces exist in these compounds. Ion-dipole forces were generated between polar
water molecules and a sodium ion. The oxygen atom in the water molecule has a slight negative charge
and is attracted to the positive sodium ion. These intermolecular ion-dipole forces are stronger than dipole
interactions because the charge of any ion is much greater than the charge of a dipole. Ion-dipole
bonding is also stronger than hydrogen bonding.
Strong Organic Acid Compounds
Further addition of a weak base such as 5% NaHCO 3 determines whether the acid is strong or
weak. If the solute is soluble in a weak base such as the said solvent, then it is a strong organic acid.
Strong acids can easily be deprotonated and can attack even a weak base such as sodium bicarbonate,
so they are soluble in this solvent. Weak acids, unlike the strong ones, do not react with weak bases.
Benzoic acid is the only solute that was observed to be soluble in both 5% NaOH and 5% NaHCO3.
Thus, carboxylic acids are strong organic acids.
++ H 2 C O3
N a
C6 H 5 COOH + NaHC O3 C 6 H 5 CO O
Balanced chemical equation of the addition of NaHCO3 to Benzoic acid
dissolved in water is because of the compounds benzene rings which break off these hydrogen bonds,
and because the water molecules involved here interrupt the van der Waals attractions between the
aniline molecules. (Clark, 2004)
Benzamide has been identified as a miscellaneous neutral compound (M) because it had been
insoluble in water and NaOH, and its solubility in HCl was unidentifiable. Miscellaneous neutral
compounds contain nitrogen or sulfur atoms and undergo hydrolysis and reduction when heated.
Benzamide, C6H5CONH2, is an amide derived from benzoic acid. It is slightly soluble in water and
hydrolyzes to form carboxylic acid and an amine under the presence of a strong acid. In this case, the
strong acid used was HCl and its reaction with benzamide (and NaOH) yielded sodium benzoate and
ammonia.
C6H5CONH2 + HCl + NaOH -> NaCHO + NH3
Benzyl alcohol and benzaldehyde have been identified as neutral compounds (N) because they
had been insoluble in water, NaOH, and HCl, but soluble in concentrated H 2SO4. Neutral compounds are
unsaturated and contain oxygen. Examples of functional groups under this include alcohols, aldehydes,
anhydrides, esters, ethers, and ketones (McMurry, 2008). Concentrated H 2SO4 is highly polar and is
capable of protonating all organic compounds containing oxygen and/or nitrogen, which then exist as
ionic salts. Compounds reacting with H 2SO4 exhibit properties of chemical change, such as heat
production, evolution of gas, or color change.
Benzyl alcohol is a primary alcohol w/ an arene group. It is very polar and cannot dissolve in
water, like all alcohols which are "protic" solvents (with a hydrogen atom attached to an oxygen atom.)
Alcohols undergoes what is known as a dehydration reaction, in where the elimination of water molecule
replaced by a pi bond between carbon atoms, forming alkenes when heated with strong acids.
London dispersion forces are the only forces that can be applied to saturated hydrocarbons
because of their weak polarity. They are generally insoluble in water because of the incapacity to break its
hydrogen bonds.
Hexane is non-polar while sulfuric acid and water are polar; therefore, there is no reaction
formed. Meanwhile, sulfuric acid adds to toluene through electrophilic aromatic substitution.
(www.mendelset.com/articles/689/properties_hydrocarbons)
References
Books:
McMurry, J. (2008). Organic Chemistry. USA: Thomson, Brooks and Cole Publishing.
McMurry,J. (2010). Foundation of Organic Chemistry. Philippines: Cengage-learning.
Smith, J. G. (2006). Organic Chemistry. New York: The McGraw-Hill Companies, Inc.
Zimmerman, I. (2003). Elements of Organic Chemistry. New York, NY: Macimlla Publishing Co.,Inc.
Internet:
Biology-online. (2005).
.on February 1,2016.
Ethylene.
Retrieved
from
http://www.biology-online.org/dictionary/Ethylene
Solubility
of
Organic
Compounds.(n.d.).
Retrieved
from
http://www.chem.ucalgary.ca/courses/351/laboratory/351expt_01_solubility.pdf on 06 February 2016.
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