CHM142-L ORGANIC CHEMISTRY 2

POST-LABORATORY REPORT (1)

Solubility Properties of Organic Compounds
Quicay, J.C , Quilo, V.M, Remo, EGM, Resurreccion J.E, Salundaga L. J
BS CHEMICAL ENGINEERING MAPUA INSTIUTE OF TECHONOLOGY AT LAGUNA

ENGR. EDEN S. ERASGA

ABSTRACT
This experiment mainly aims to determine the solubility of organic compound as it manifest an
important key concept in giving useful information on its structure and composition. In the
experiment the solubility of 13 compounds namely ethanoic acid, ethanol , 2-propanone ,
ethoxy ethane , 1-butanal, methanamine, alanine, sodium acetate, benzoic acid, phenol, aniline
acetophenone and cyclohexane was analyzed qualitatively using solvents water, 5% sodium
hydroxide, 5 % sodium bicarbonate, 5% hydrochloric acid, di-ethyl ether and water. The
observations on the solvents used is showed in Table 1.1 and was analyzed for their possible
classification
INTRODUCTION
Solubility is the degree of how much solute can be dissolved in a given amount of
solvent that can be measured in mg per 100 mL solvent. It is a property that can be used in
identifying the type of functional groups present in an unknown compound. Its application can
be widely seen in the fields of chemistry, physics, food sciences, pharmaceuticals and biologics.
In the field of medicine, a substance solubility becomes particularly significant, since sometimes
it is a major factor in regulating drug bioavailability. In different types of units, the solubility of a
substance can be defined, each of which represents an expression of how much solute is
dissolved in a solution at a given temperature.

However, the solubility of each compound in constant temperature is distinct since it is

affected by numerousparameters such as steric factors, branching, its molecular weight,
existence of functional groups, pH and electron withdrawing groups . The energy needed to
interact between the molecules or ions of the solute in the dissolution of a compound comes
from new interactions between the solvent and solute (Smith, 2008). In solvents of similar
intermolecular forces, polar compounds will dissolve in polar solvent, likewise non-polar
compounds will dissolve in non-polar and weakly polar will only dissolve in weakly and non-
polar solvents. This concept follows the idea of “like dissolves like”. Two different types of
solvents are water and organic liquids. Water is highly polar, as hydrogen can be linked to a
solute e.g carbon tetrachloride (CCl4) and hexane [CH3(CH2)4CH3] are numerous organic
solvents that are either nonpolar, or weakly polar, almost like ether (CH3CH2OCH2CH3).

Strong electrostatic forces hold the ionic compounds together, so they need very polar
solvents to break those forces. Many ionic compounds are water-soluble but in organic solvents
are insoluble. To dissolve an ionic compound, many weaker ion – dipole interactions must
replace the strong ion – ion interactions. Moreover, in organic solvents most organic compounds
are soluble (like dissolves like). An organic compound can only be water soluble if it contains a
polar function group able to bind hydrogen to the solvent for each of the five C-atoms it
contains. In other words, an organic water-soluble compound has a functional group containing
O and N that is solubilizing the nonpolar backbone of the organic compound.

Solubility is dependent vigorously in temperature, with respect to this parameter, the

solubility of gases implies an inverse relationship, since increasing the temperature will make an
increase in kinetic energy which break IMFAs and make the gas molecules escape solute-
solvent attraction in the solution. However, in liquids increasing the temperature will also
increase the kinetic energy with this relationship it permits the solvent molecules to more
effectively break apart the solute molecules that are held together by intermolecular attractions.

The established compound attractive forces tie together the molecules or particles of a
pure solute and a pure solvent. Solution building includes molecular intermixation: to "expand"
solute and solvent compounds some other attributing forces need to be separated to allow for
interpenetration. The formulation of solutions requires breaking down solvent-solute
(intermolecular) forces, which require an energy supply into the system. In addition, breakdown
of such intermolecular solvent-solvent forces requiring energy input into the device. The
development of the desirable (intermolecular) solvent-solvent zinterparticle forces. This entails a
release of energy and must compensate for the mechanism for the energy input required to
break down the current interparticle solute-solute and solvent-solvent forces (McMahon,
Khomtchouk, & Wahlestedt, 2017).

This experiment aims to interpret the organic structure using simple solubility test that is
extremely useful in providing details on the type of functional groups present, to give more
specific information on the existence of these functional groups and create some deductions on
the molecular size and organic structures based on its solubility on certain solvents such as 5%
NaOH solution, 5% NaHCO₃ solution, 5% HCl solution, and cold concentrated H2SO4 (Shriner,
Hermann, Morrill, Curtin, & Fuson, 2004). Moreover, this experiment also aims to study the
factors influencing the solubility of organic compounds and be able to generalize these concepts
in solubility and how these factors imparts on the similarities and differences on their solubility

MATERIALS AND METHODS

The qualitative analysis on determining the classification of compounds can be
accomplished using solubility test in certain solvents such as distilled water, diethyl ether, 5%
NaOH, 5% NaHCO3, 5% HCl, and concentrated H2SO4. In performing the solubility test in water,
4 drops of liquid sample or a weight of 0.1 g of solid sample were added to the 2 mL the of
distilled water solvent in a test tube. If the observed solubility is water soluble, the same set-up
for solubility test in water is also applied in Diethyl Ether Test. The diethyl ether-insoluble
compounds belongs to Class S2. However, diethyl ether-soluble solutions needed to be tested
with pH paper, in addition the pH of water is also tested to prevent misleading results. Solutions
with pH <7 it belongs to Class SA. For solutions that are too basic can be classified to Class SB.
For solutions with neutral pH belongs to Class S1. For water-insoluble substances, 5% NaOH
Test was performed . Using the same set-up , NaOH-soluble solutions was then tested with 5%
NaHCO3 Test. In this test, mixing the substance and solute is inhibited and appearance of
bubbles were also observed. Substances that had bubbles (soluble) is classified to Class A1.
Substances that was insoluble is under the Class A2. For NaOH-insoluble substances, 5% HCl
test was performed. Samples which are HCl-soluble belongs to Class B while samples which
are HCl-insoluble was further mixed with concentrated H2SO4 in a dry test tube and were
distinguished if it is soluble or insoluble. H 2SO4-soluble samples belongs to Class N while
H2SO4-insoluble samples belonged to Class I. Some H2SO4-insoluble samples that contains
nitrogen or sulfur belongs to Class MN.The sample were stirred with the aid of glass rod to be
determined as soluble or insoluble. In this experiment, in order to achieve the objectives of the
experiment the samples to be used are follows (1) Ethanoic Acid, Ethanol, 1-butanal ,
Methanamine, Alanine, Sodium Acetate, Ethoxy, Ethane, Benzoic Acid ,Phenol, Aniline,
Acetophenone, and lastly the cyclohexane.

Figure 1.1 Solubility Test

DATA AND RESULTS

Table 1.1 shows the summary of general observations in the first set of aforementioned
compounds in water and diethyl ether. The solubility of compounds on these two solvents will
venture a conclusion on its general structure, however it will not yet give further details on its
specific structure. In line with this, the acidity and basicity of organic compounds is then
observed using litmus paper test to determine if the unknown compounds is partially or
completely soluble in water from this, it can narrow the classification of organic compounds into
S2 as salts of organic acids amine hydrochlorides, Sa as monofunctional carboxylic acids with
less than or equal to five carbons S b as a monofunctional amines with less than or equal to 6
carbons and S1 as monofunctional aldehydes , alocohols, ketones or nitrile.

Upon the addition of four drops of liquid sample, ethanoic acid imparts a clear
homogenous liquid when it undergo water and dimethyl test, to give further information on its
classification, the pH observed in the litmus paper test is less than the neutral (pH 5) with this it
can be conjectured that this compound belongs to solubility Class Sa or a class of monofunctional
carboxylic acids that has less than or equal to 5 carbon. Results obtain agrees since Ethanoic
acid is a hydrocarbon derivative on which 1 or greater than 1 H atoms is substituted by carboxyl
group, their strong hydrogen bond makes it capable to be soluble at organic solvent such as
diethyl ether.

Table 1.1 Name of Sample: Ethanoic Acid

Solubility Tests +/- Observations

Water + The solution was observed as a transparent, colorless, or clear liquid.
Diethyl Ether + A transparent, colorless or clear liquid was also observed.
pH 3 The solution is acidic due to the pH is less than the neutral (pH 5).
Solubility Class: Class SA
Using the same method in determining the solubility, Ethanol, 2-propanone, ethoxy-
ethane and 1-butanal has been grouped into another classfication of organic compounds. The
absence of precipitate, colorless, clear, and transparent appearance in the solution is a good
indicator that the aforementioned compounds is readily soluble in water and diethyl ether, to
give further specific details litmus paper test is done and results have shown that the pH of this
organic compounds is considered neutral. In line with this, it can be deduced that these
compounds can be classified into Class S1 or compounds that is monofunctional ketones,
alchohols, aldehydes, esters, amides and nitriles with carbons having less than or equal to five.

Name of Sample: Ethanol

 Solubility Tests +/- Observations
Water + A clear, transparent, colorless solution was obtained.
The appearance of transparent, colorless or clear liquid was observed as
Diethyl Ether +
same as it dissolves in water.
pH 6 The pH of the solution is basic since it is greater than the neutral pH.
Solubility Class: Class S1

Name of Sample: 2-propanone

Solubility Tests +/- Observations
Water + A clear transparent, colorless solution was observed.
Diethyl Ether + Precipitate free and a transparent, colorless solution was observed.
pH 5 The pH of the solution is neutral, the litmus paper did not change its color.
Solubility Class: Class S1

Name of Sample: Ethoxy Ethane

Solubility Tests +/- Observations
Water + A transparent, colorless solution was observed.
Diethyl Ether + A transparent, colorless solution was observed.
pH 5 The solution is neutral because the litmus paper did not change its color.

Solubility Class: Class S1

Name of Sample: 1-butanal

Solubility Tests +/- Observations
Water + A transparent, colorless liquid, is observed
The solution is clear and has no presence of precipitates indicating a
Diethyl Ether +
homogenous solution
pH 4 The pH obtained is neutral
Solubility Class: Class S1
Even though methanamine implies the same observation, the basicity of methanamine
depart it from other classification with observed pH of 12 in the litmus paper test. As a result,
this compound is classified as Class Sb that includes organic compounds that are
monofunctional amines. On the other hand, alanine and sodium acetate both give a clear
pellucid solution in H2O, this observation implies that these two compounds are highly soluble
in water. However, the formation of two heterogenous layers of white particles is high indicator
that alanine and sodium acetate is insoluble in water this observation, deviates the pH of
these two compounds for being tested in litmus paper test. This implies that the compound
can be clearly classified as Class S2, this classification includes salts of organic acids. amino
acids , and polyfucntional compounds containg hydrophilic functional groups these group also
includes the polybasic acids and polyhydroxyl compounds.
Name of Sample: Methanamine
Solubility Tests +/- Observations
Water + A transparent, colorless solution was observed.
Transparent but slightly slightly turbid in color but still exhibit a clear liquid
Diethyl Ether +
solution
pH 12 The pH of the solution is basic since it is greater than the neutral pH.

Solubility Class: Class SB

Alanine and sodium acetate both give a clear pellucid solution, this observation implies
that these two compounds are technically soluble in water. However, results of diethyl ether
test both gives an observation that these two compounds are both insoluble at organic
solvents due to the presence of white precipitate that agitated at the bottom of the tube. Using
these observations these two compounds are associated in the classfication of Class S2 that
includes polyfunctional compounds that has hydrophilic groups, salts of organic acids, amine
hydrochlorides and amino acids.

Name of Sample: Alanine

Solubility Tests +/- Observations
Water + A clear ,pellucid, colorless solution was observed.
A transparent, colorless with white precipitate located at the bottom of the
Diethyl Ether -
tube has been observed

Solubility Class: Class S2

Name of Sample: Sodium Acetate
Solubility Tests +/- Observations
Water + A clear transparent, colorless solution was observed.

Diethyl Ether - Some sodium acetate did not dissolve and remained at the bottom.
Solubility Class: Class S2

If the organic sample is insoluble in water it will undergo another test, instead of using
diethyl ether a strong base (NaOH) sodium hydroxide is used to determine its respective
classification. The ability of the organic compound to dissolve in NaOH can be classified into
Class A1 , class A2, Class B, Class N or Class I. On the experiment, Benzoic acid and phenol
did not dissolve completely on water creating two layers of liquid for phenol and a white
precipitate for benzoic acid , to further specify its classification NaOH is used, these two
compounds both give a clear pellucid solution indicating that they are soluble in this strong
base . However for more specific details 5% sodium carbonate is used but since +they are not
completely miscible with sodium bicarbonate it is classified as class A2 or weak organic acids.

Name of Sample: Benzoic Acid

Solubility Tests +/- Observations
A transparent liquid solution was observed. Some benzoic acid did not
Water -
dissolve and leave a white precipitate remained at the bottom.
5% NaOH + A transparent, colorless solution was observed.
Some benzoic acid did not dissolve and leave a white precipitate remained at
5% NaHCO3 -
the top.

Solubility Class: Class A2

Name of Sample: Phenol

Solubility Tests +/- Observations
Phenol did not dissolve in water. Phenol is immiscible with water; it creates a
Water -
two liquid layers. The phenol stayed at the bottom.
5% NaOH + A transparent peach color solution was observed.
Phenol did not dissolve; it is also immiscible with the in 5% NaHCO 3. Two-layer
5% NaHCO3 -
of liquid was also observed. The phenol stayed at the bottom.

Solubility Class: Class A2

Aniline on the other hand are both insoluble in water and sodium hydroxide, from this
observation, its transparent peach color solution in 5% hydrochloric acid makes it classified into Class B
or the compounds of aliphatic amines with 8 or more carbons. Same with Aniline , Acetophenone also
gives behavioural insolubility at water and sodium hydroxide the difference is, it is also insoluble in
hydrochloric acid and to verify if its Class N or Class I, five percent of hydrosulfuric acid is used and
gives a clear dark yellow solution implying that this compound belongs to Class N or the group of
alcohols, aldehydes, ketones, esters with one functional group and has less than nine carbons. The last
organic compound tested gives an insoluble behaviour at all of the solvents used implying that this
compound is non-reactive and belongs to the Class I or class of saturated hydrocabons.

Name of Sample: Aniline

Solubility Tests +/- Observations
Aniline did not dissolve in water and a drop of yellow colored anilines in the
Water -
water was observed.
 Two liquid layers was observed in 5% NaOH, for that the brownish colored
5% NaOH -
aniline stayed at the top.
5% HCl + A transparent peach color solution was observed.

Solubility Class: Class B

Name of Sample: Acetophenone

Solubility Tests +/- Observations
The solution of acetophenone in water was slightly translucent or slightly
Water -
cloudy.

5% NaOH - Acetophenone did not dissolved in 5% NaOH and appeared a cloudy solution.
Acetophenone did not dissolve in 5% HCl, for that the solution was slightly
5% HCl -
cloudy. Some bubbles appeared at the side of the tube.
Concentrated Acetophenone dissolved in the concentrated H 2SO4, the solution changed its
+
H2SO4 color to a transparent dark yellow.

Solubility Class: Class N

Name of Sample: Cyclohexane
Solubility Tests +/- Observations
Two transparent liquid layers were formed. Cyclohexane is immiscible with
Water -
water.
5% NaOH - Two transparent liquid layers were formed.
Cyclohexane was still undissolved with two transparent liquid layers were
5% HCl -
formed.
Concentrated
- A cloudy two liquid layers were formed.
H2SO4

Solubility Class: Class I

DISCUSSION

The solubility of organic compounds is a concrete measurement of the maximum

amount of solute that can be dissolved in a certain amount of solvent. It is a physical property
that can be easily recognized in any change in composition thus, it is a convenient tool that can
be used in identifying the presence of the functional groups. With the aid of this property, the
qualitative analysis on determining the classification of compounds can be accomplished using
solubility test in certain solvent and is governed by several factors such as molecular weight,
steric factors, the functional groups present, electron donating and withdrawing groups, acidity
and basicity.

DISSOLUTION PROCESS

The underlying property that favors the formation of solution is accompanied by solute-
solute, solvent-solvent and solute-solvent interactions, the solution formation is a spontaneous
process that is not energy requiring however this can only be achieved if the relative strengths
of IMFA between solute and solvent species in a solution are greater to those other separated
components. To provide space for the solute particles, the particles are pushing apart in
solvent-solvent interactions thus, this process is energy requiring or endothermic. Similarly,
solute-solute interaction is also endothermic since energy is required with the purpose of
overcoming the forces in the attraction between the solute particles. However, the bond that
forms between solute solvent interactions are exothermic or energy releasing and solvation will
only occur if the energy released in the formation of bond is relatively greater than the energy
required to break the bonds in dissolution(Figure1.2).
 Figure 1.2 The Dissolution process

Heat is required in breaking bonds that hold the molecules in the solid together (solute-
solute and solvent-solvent) this relationship makes the process endothermic. At the same time,
the formation of solute-solvent bonds gives off heat and is therefore exothermic. If the heat
extricated in the dissolving process is higher than the heat required to break the solid apart, the
net dissolving reaction is exothermic. Moreover, in order for a homogenous solution to be
formed the intermolecular attractions that exist between solute particles should be the
same. On the other hand, if the intermolecular attractions that exist between solute particles are
different compared to the intermolecular attractions between solvent particles it is unlikely that
dissolution will occur. These concepts demonstrate the thumb rule in organic chemistry that “like
dissolves like” and elucidate the reasons why some compounds do not mix homogenously.
Based upon the thermodynamic concept behind the dissolution process the observable change
in dissolution is also governed by such factors. In Table 1.1 shows a summary of detailed
observations in the first set of aforementioned compounds in water and diethyl ether.

NATURE OF SOLUTE AND SOLVENT

SOLUBILITY IN WATER

Water is highly polar that can form hydrogen bonding tremendously unlike on other organic
solvents; this polarity allows weak attractions between polar molecules to form bonds from
individual water molecules. Using this solvent to determine the solubility of organic compounds
will deduce its property if it is water soluble or not. Generally, there are some conditions for an
organic compound to be dissolved in water, (1) it must contain a polar functional group that is

capable of forming hydrogen bonds with water. (2) Should be small enough for it to dissolve in
water and in addition organic compounds in its ionic form could also dissolve in water.
 As a rule, organic compounds with one functional group having carbon atom that are ≤ 3
are soluble in water. This explains why compounds that contains greater than or equal to 5 are
generally are insoluble and those with 4-5 carbon atoms are marginal. Low molecular-weight
amines and oxygen-containing compounds are generally water soluble. The ability of water to
dissolve organic compounds will depend on the nature of the functional group present. Mostly,
organic compounds that are generally soluble in water are the compounds that contains
hydroxyl group or a carboxylic acid, aldehydes, ketones. Ester, amides and nitriles can also
form hydrogen bonds in water however the absence of hydrogen atom to form a hydrogen
bond on the oxygen atom of water makes them less water soluble than carboxylic acids and
alcohols. On the other hand non-polar groups such as alkenes alkynes and alkanes are
generally insoluble to water since these compounds do not meet the criterion in the thumb rule
of “like dissolves like” this non-polar characteristics makes them insoluble in water.

To illustrate the trend in the solubility of organic compounds in organic acids

a. Butane < b. 1-butanol < c. 1,4-butanediol

d. Isopropyl alcohol < e. methanol

Methanol has the least number of carbons with a hydroxyl group making it extremely
soluble in water among the given compounds.Since isopyopyl alcohol contains a higher
number of carbon atoms it is less soluble than methanol . Consequently, 1.4 butanediol is more
soluble than 1-butanol since diols are compounds with 2 hydroxyl group that is capable of
hydrogen bonding making it more soluble than the primary alcohol of 1-butanol even the
carbon atoms are larger than 1-butanol. Lastly, butane being the only non-polar among the
compounds present in the examples are the least likely to form a solution in water since it
doesn’t contain any functional group that will interact to water to form solvent.

The size of the organic molecule is a huge factor in depicting the solubilty of organic
compounds in water. Phenol for example contains hydroxyl group that is highly water soluble
however it does not dissolve in the experiment since its size is greater than 5 carbons, large
enough for it to become water insoluble. In summary, comparing water to other organic solvents
the solubility of organic compound still obeys the like dissolves like rule, mostly if the solvent is
organic it will be able to solve nonpolar compounds, likewise water which is highly polar solvent
will dissolve polar organic compounds.

SOLUBILITY IN DIETHYL ETHER

Figure 1.3 Structure of diethyl ether

Diethyl ether is the second solvent used in the solubility test to determine if the compounds
dissolved in water is highly polar. Its purpose lies to determine if the compound is an organic
(aldehyde, ketone or carboxylic acid) or merely an inorganic salts. The structure of this
compound (Figure 1.3) does not contain a hydrogen bond that will be broken up to dissolve the
solute and polar substances preferably dissolve in diethyl ether because of the dipole moment
that it contains. Basically, hydrogen bonds can be form to nonbonding electron pairs of the
oxygen atoms of ether resulting for polar compounds to become hydrogen bond donors when
dissolve in diethyl ether. (Ouellette, 2015). On the experiment results have showed that alanine
and sodium acetate both didn’t dissolve in diethyl ether. Sodium acetate is an inorganic salt that
has no hydrocarbon portion that would interact with the oxygen atom of the ether, likewise, the
structure of alanine is an amino acid that has lot of alkyl groups surrounded making it incapable
to form bond with the oxygen atom of the ether. To further narrow down the classification of
organic compound that dissolved in both water and diethyl ether, litmus paper test is used.
Compounds that are acidic are most likely classified as carboxylic acids , basic compounds are
most likely to be classified as amines and lastly compounds that gives neutral pH are probably
an alcohol, ketone or aldehydes.Diethyl ether having a boiling point of 34.6 degrees Celsius is
extremely flammable and could evaporate readily in room temperature thus, heating is not
applied for testing diethyl ether.

PH AND TEMPERATURE AND ITS EFFECT ON SOLUBILITY

Temperature has a strong influence in the solubility of organic compound in a certain

solvent. It affects the solubility of the solute for all liquids, solid and gases. Temperature and
solubility has an inverse or direct relationship depending on the type of solution
process.Generally, increasing the temperature in an exothermic solution process will decrease
the solubility of the solute in the solvent that implies an inversely proportional relationship. On
the other hand, temperature and solubility has a direct relationship if the solution process is
endothermic, thus increasing the temp will also increase the solubility. Example of exothermic
solution process is the solubility of gases in liquids, the interactions of gas molecules to the
liquid solvent releases heat, this heat will serve as a thermal energy that overcomes the
attraction between gas and liquid molecules, thus making the process exothermic.

Altering the pH of the solution has a great effect on the solubility of one’s solute . The pH
of a solution will affect the solubility of any substance whose anions are basic. Basically the
more basic an anion is the more soluble the compounds will be an acidic solution. On the
experiment performed, sodium hydroxide, sodium bicarbonate and hydrochloric acids with 5
pecent v/v concentration is used. Each compound can be more soluble in acidic or in basic
conditions than in water that reflects the presence of an acidic or basic functional groups in the
water-insoluble compounds. Based on the results obtained the turbidity and formation of
precipitate can be an indicative of higher solubility in acid or base than in water. The enhanced
solubility in both acidic and basic conditions can be utilized to identify what kind of functional
group is present in a compound. The solubility of organic compounds that didn’t dissolved in
water is tested on sodium hydroxide on which strong and weak acids such as carboxylic acids
and phenols can be converted into salts this conversion indicates that this compounds are
soluble sodium hydroxide. On the other hand water insoluble compounds that didn’t dissolved in
sodium hydroxide can be tested on hydrochloric acids. Assesing the possibilities that may occur
based on the performed test is presented on the results in Table 1.1.
 The presence of carboxylic acids can be determined if the compound dissolved in
sodium hydroxide is also soluble to sodium bicarbonate, the presence of bubbles and
effervescence indicates the formation of this equation

Equation 2.1

On the experiment even the benzoic acid contains carboxylic acid, it didn’t dissolve in
sodium bicarbonate since any carboxylic acid with a high molar mass could not be dissolved
completely in aqueous medium, thus evolution of gas or bubble formation can only be observed.
In line with this phenol on the experiment did not dissolve on sodium bicarbonate this is evident
from the observation on which two-layer of liquid has formed. This implies equation 2.5

Equation 2.2

The presence of amino functional groups can be identified if the compound exhibits a good
solubility behavior in hydrochloric acids, this happens because amines are organic bases that
can readily react to dilute acids, this reaction would yield to the formation of water soluble
ammonium salts. The basicity of amines is due to the presence of unshared pair of electrons
that can be shared readily to other atoms, this unshared pair of electrons produces a high
electron density around the nitrogen atoms. To illustrate the basicity of amines towards
hydrochloric acid the following amines are given below.

a. Butanamide < Diphenylamine < d. 4-methylaniline

 < e. Benzylamine < b. Pentylamine

Generally, the greater the electron density, the higher the basicity of a molecule is. Groups
that donate or supply electrons is capable of increasing the basicity of amines, to be specific
groups that decrease the electron density around the nitrogen decrease the basicity of the
molecule. Based on the given examples Pentylamine exhibits the highest basicity since the alkyl
groups of this aliphatic amines donate more electrons to the more electronegative nitrogen. The
inductive effect on the nitrogen of pentlyamine makes the electron density greater than other
nitrogens of 4 given compounds. The delocalization of electrons between the nitrogen and
oxygen in butanamide makes butanamide the weakest base among the given compounds. The
aromatic rings in diphenyl amine and 4-methylaniline that resonates the electrons in nitrogen

makes it a weaker base than benzylamine In summary, pentlyamine is the most soluble in the
hydrochloric acids solution.

Basically, all organic compounds compounds that are insoluble in 5% HCl are tested
with concentrated sulfuric acid (H2SO4). Concentrated sulfuric acid has the ability to
protonate organic compounds that may contain oxgen or nitrogen. This is attributable to the fact
that sulfuric acids are highly polar that can dissolved protonated compounds. The dissolvation
happens due to the presence of carbon-carbon double bonds, oxygen, nitrogen or sulfur in the
unknown compound. The solution process of compounds in hydrosulfuric acid is an exothermic
process on which large amount of heat is released on the solution. All organic compounds that
has an alkene functional groups, or nitrogen or oxygen atoms can dissolve readily in this
solution and those that are insoluble can be considered as an alkanes, alkyl halide or an
aromatic compound. The presence of multiple functional groups in an organic molecule may
cause different solubility properties from the compounds that are monofunctional likewise the
presence of one or more electron withdrawing groups may strongly influence the solubility
properties of certain compound.
 Molecular geometry is another factor that may influence the solubility of an organic
compound in a certain solvent however solubility determines more the nature of the surface
than the shape of the molecule. If the surface is polar, it will be approached by a polar solvent,
leading to good interaction energy and perhaps good solubility. Only when it is difficult to fill the
surface with water molecules does the actual shape itself come into play: an impractical shape
and size could cause some discomfort and therefore lower energy and solubility for solvation
(Ouellette, 2015). The simpler the structure of the molecules the better it dissolves. Lastly,
molecular size also implies a great effect on solubility, for example compounds with carbons
higher than 5 are mostly insoluble to water. In addition, the increased in branching and position
of functional groups on the center of the molecule increases solubility.

The underlying principle of like dissolves like in general chemistry on solubility is the
thing that presides over the solubility concepts in organic chemistry. However, general
chemistry focuses on the solubility rules of most ionic and inorganic compounds that mostly
dissociate in a polar solvent such as water and the solubility of gases according to Henry’s law.
They are governed by several factors mostly by pH, temperature and pressure for gases. On
the contrary, the concepts that lies beneath organic chemistry digs deeper on the molecular
structure of compound, its polarity, the nature of solute and solvent , effects of steric effects and
the electron withdrawing / donating group, type of functional groups present, effects of
resonance in solubility etc. The deep analysis of organic chemistry in the structure and nature of
functional group of a compound deviates it from the solubility concepts in general chemistry.
However, both of the concept in general and organic chemistry uses the principle of “like
dissolves like” similarly, temperature, and pH both imply a strong influence in the solublity
concepts being studied in the two separate fields. Solubility tests are significant because it could
indicate the polarity and size of an unknown compound and can also detect the presence of
acidic or basic functional groups with the aid of this test valuable information about the nature of
compound can be ventured.

CONCLUSION
Solubility is a physical property that can be easily recognized in any change in
composition thus, it is a convenient tool that can be used in identifying the presence of the
functional groups. The aim of the experiment is to apply qualitative analysis on determining the
classification of compounds that can be accomplished using solubility test and to identify the
factors that contribute to solubility. In order to uphold these objectives, the 13 aforementioned
compounds was analyzed using different solvents such as distilled water, diethyl ether, 5%
NaOH, 5% NaHCO3, 5% HCl, and concentrated H2SO4..Results have shown that ethanoic acid
belongs to class Sa. The basicity of ethanol , ethoxy ethane 1-butanal and 2-propanone that
dissolved in both ethyl and diethyl ether is conjectured in the classification Class S1, Moreover,
the water-soluble compounds: methanamine, sodium acetate and alanine that is insoluble in
diethyl ether is classified as Class S2. The ability of benzoic acid and phenol that dissolved in
strong base is classified as Class A2. Acetophenone that is only soluble at concentrated sulfuric
acid belongs to Class N, and Aniline that is only soluble at hydrochloric acid belongs to the
classification Class B, and lastly cyclohexane that is insoluble to all solvents belongs to Class I.
Upon completion of the experiment it is sensible to conclude that solubility test is still
appropriate method in determining the classification of an unknown compound however if
careful attention is not performed in qualitative organic analysis, inconclusive positive and
negative tests could be interpreted incorrectly and an illogical approach on the classification of
compound may be acquired yielding to misclassification.

APPENDIX
Compound Structure Solubility behavior
In water, 1-chlorobutane is insoluble
since it is a haloalkane. It is insoluble in 5
percent solution for sodium hydroxide, 5
1-chlorobutane
percent solution for hydrochloric acid
and 96 percent solution for sulfuric acid.
So, 1-chlorobutane is in Class I solubility.
Hexane is insoluble in water, 5 % sodium
hydroxide solution, 5% hydrochloric acid
Hexane solution and 95% sulfuric acid as
saturated hydrocarbon. Hexane falls in
Class I solubility
Because it contains less than five carbon
atoms, 1-butanol is soluble in water. It is
1-butanol soluble in ether, and the color of litmus
does not change in its aqueous solutions.
1-Butanol is class S1 in solubility
Benzoic acid is as strong organic acid
insoluble in water, soluble in 5% sodium
Benzoic acid hydroxide solution and soluble in 5%
sodium bicarbonate solution. Benzoic
acid therefore is class A1 in solubility
 Methyl propanoate is water soluble,
since it contains fewer than five atoms of
Methyl propanoate carbon. In ether, it is soluble, and its
aqueous solutions do not change the
litmus color. It is Class S1 in solubility

Table A the structure and solubility behavior of some compounds

REFERENCES

 Ouellette, R. J., & Darwin J. D. (2015). Principles of Organic Chemistry.

 Harper College Retrieved from:

http://dept.harpercollege.edu/chemistry/chm/100/dgodambe/thedisk/qual/solubil.html

 Identifying an Unknown Compound by Solubility, Functional Group Tests and Spectral

Analysis. Cengage Learning Retrieved from:
http://www1.udel.edu/chem/CHEM322/Handouts/unknowns_lab_handout.pdf
 Mohrig, J. R., Hammond, C. N., & Schatz, P. F. (2010). Techniques in organic chemistry: miniscale,
standard taper microscale, and Williamson microscale. New York: W.H. Freeman.