Name: Dagondon, Vanessa Olga

Date Performed: February 2, 2015

Sanchez, Diandra Dawn

Date Submitted: February 9, 2015

Solubility Behaviour of Organic Compounds

Experiment 1
I.

Objectives

The purpose of this experiment is to test selected organic compounds in various

solvents and to be able classify the said compound in their respective solubility classes. The
relation between the results of the solubility tests done on a particular compound and its
structure must also be identified.
II.

Results & Discussion

Solubility plays an important role in identifying the composition or structure of

unknown organic compounds. Though not as transparent as spectroscopy techniques,
solubility tests provide information and key ideas about the possible structural features an
organic compound exhibits. This is so because the solubility behaviour (soluble, insoluble) of
an organic compound on a certain solvent is determined by its structure.
Twelve (12) organic compounds were utilized and were tested on six (6) solvents
H20, ether, 5% NaOH, 5% NaHCO3, 5% HCl, Conc. H2SO4 whilst following an
interconnected diagram that would lead on to the classification of these organic compounds
to their respective solubility classes.
The table (see figure 1) below summarizes the results of the solubility tests done. The
symbol (+) signifies that the organic compound is soluble to a particular solvent and the
symbol (-) signifies otherwise. The following are the organic compounds tested with
explanation on their solubility behaviour on different solvents:

Acetone
1. Water was the first solvent used to test all the organic compounds including
acetone. Acetone was found out to be miscible in water. This immediately gives an
idea that acetone is a polar compound in accordance to the facts that water is also a
polar solvent; and the rule of thumb, like dissolves like. The structure of the acetone
is responsible for its polarity. As seen below (see fig. 1), there is a double bond
between carbon and oxygen, and thus, the oxygen has two pairs of unshared electrons
which in turn makes that portion of the molecule to be highly negative and the
opposite portion to be positive. This difference of charges around the molecule makes
it polar. The next solvent that was used was ether and again, acetone was found to be
miscible in it. Ether is a non-polar organic solvent. Since acetone is miscible in it,
three things can be deduced: there is interaction between the hydrocarbons of the
compound and that of the ether which confirms that acetone is indeed organic;
acetone which was said to be polar is not that extremely polar since it is miscible in a
Page 1 of 5

non-polar solvent; lastly, this automatically classifies acetone as an organic compound

belonging to the solubility class S1 Ether Soluble. Compounds belonging to the
solubility class S1 are mono-functional containing 6 carbons or fewer. Acetone has
only one functional reactive site and contains only 3 carbons.

Aniline
2. Aniline was immiscible in water and thus, categorizing it as a nonpolar
compound. Since it is immiscible, anilines solubility must be tested in 5% NaOH. As
a strong base, when added to an organic compound, it (5% NaOH) could detect the
presence of acidic functional groups. In this case, aniline was found out to be
immiscible in 5% NaOH which means that it is not acidic and therefore must be
tested in 5% HCl to detect the presence of basic functional groups. Aniline was
miscible in the 5% HCl. This means that there was an acid (5% HCl) base (Aniline)
reaction that formed an organic salt which is readily soluble in water. This test labels
Aniline as an HCl-soluble (B) Basic Compound. Aniline is an example of an amine or
organic derivatives of ammonia. Taking a look at its structure, aniline has a lone pair
of electrons on its nitrogen atom making it basic.

Benzyl Alcohol, Benzaldehyde and Benzamide

3. Benzyl Alcohol was insoluble in water in experimentation. To be exact, Benzyl
alcohol is partially soluble in water. Benzyl alcohol is still an alcohol and therefore
has an OH group in its structure thus, making it polar and supposedly soluble in
water. However, since it has a large benzene ring in its structure, its solubility in
water is only partial. Benzaldehyde and Benzamide were also insoluble in water
because of the same reason as Benzyl Alcohol. The next test that was on 5% NaOH
and 5% HCl and all three were insoluble in the said solvents. Therefore, none of them
were acidic or basic. All, then, were tested on conc. H 2SO4 except for Benzamide
because it contains Nitrogen and will automatically be a part of the Miscellaneous
Neutral Compound (M) solubility class. The conc. H 2SO4 solvent will distinguish
carbonyl compounds and purely hydrocarbon compounds. Carbonyl compounds are
compounds having a carbon atom double bond with oxygen. Example of carbonyl
compounds are aldehydes and ketones. In this case, all three compounds reacted with
the conc. H2SO4 exhibiting evolution of gas, formation of precipitate, change in color
and thus, they soluble in the solvent. What conc. H2SO4 does is it protonates the
compounds (Benzyl Alcohol and Benzaldehyde, which all contains oxygen) so they
exist as ionic salts and since, conc. H2SO4 is a polar solvent, it will dissolve the ionic
salts and will cause by products such as precipitates, change in color and, etc. These
organic compounds are labelled as H2SO4- soluble Neutral Compound (N).

Benzoic Acid
4. Benzoic Acid is partially soluble in water. This is due to its large benzene ring in
its structure. It is then tested on 5% NaOH but it is expected that it will be soluble
since the compound is an acid and therefore, will form an organic salt that is soluble.
As expected, it was soluble and was then tested on 5% NaHCO 3. Adding this solvent
will test the extent of the compounds acidity. If the compound is indeed a strong acid,
Page 2 of 5

a neutralization reaction will occur but if the compound is just a weak acid, then no
neutralization will occur because NaHCO3 is a weak base and will only react
completely with a strong acid. Benzoic acid is a weak acid and therefore, it is not
soluble in NaHCO3. This classifies Benzoic acid under NaHCO3- insoluble (A2).
Organic compounds classified under this class are most like to be phenols having a
hydroxyl group bonded to an aromatic ring just like Benzoic acid.

Ethyl Alcohol
5. Ethyl alcohol was found out to be soluble in water. This behaviour is due to the
stronger polarity of its hydroxyl group compared to its non-polar carbon chains. It
was then tested with ether and was again soluble in it. Just like acetone, Ethyl alcohol
is under the solubility class S1.

Hexane
6. Hexane isnt soluble in water because Hexane is a non-polar compound. It was
tested on 5% HCl and 5% NaOH and was again insoluble in the said solvents. Hexane
has neither Nitrogen nor Sulfur and therefore, must be tested with conc. H 2SO4. There
was no reaction with H2SO4 and thus, it is insoluble. Hexane, then, is classified as
H2SO4 insoluble Inert compound (I). Saturated hydrocarbons, haloalkanes, and
other deactivated diaryl ethers belong to this class. Hexane is an example of a
saturated hydrocarbon.

Phenol, Tert- butyl chloride, Toulene

7. Phenol (hydroxybenzene), Tert-butyl chloride and Toluene all tested as insoluble
in water, 5% NaOH and 5% HCl. As all of them have neither Nitrogen nor Sulfur,
they were then tested using concentrated H2SO4. When tested with the concentrated
H2S04, both Phenol and Tert-butyl underwent a change in color, with Tert-butyl being
the only one of the two to have bubbles form from the reaction. Although both did
have a change in color, there were definite lines in between the samples and the
concentrated H2SO4, making both insoluble in the solvent. On the other hand,
Toluene experienced neither change in color nor having formed bubbles, but it was
still insoluble in the concentrated H2SO4. It can then be concluded that all three
samples are Inert Compounds.

Sucrose
8. Sucrose, or commonly known as table sugar, readily dissolved in water. As the
case, it was then tested with ether. Although sucrose is soluble in water, it was
insoluble in ether because sucrose is extremely polar because it has a lot OH group,
which are polar, as seen in its structure. This makes it a part of S2.
9.
10.

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11.

Com
pound

20.

29.

12.

Acet
one

Structur 13.
H 14.
e 15.
5 16.
5 17.
5 18.
C
e
20
ther
%
%
% HCl
onc.
NaOH NaHCO
H2SO4
3
21.
22.
+ 23.
+ 24.
25.
26.
27.

28.

S
1

Anili
ne

30.

31.

32.

33.

38.
Benz
yl Alcohol

39.

40.

41.

42.

47.
Beza
ldehyde

48.

49.

50.

51.

56.
Benz
oic Acid

57.

58.

59.

60.

+ 61.

65.

66.

Benz
amide

19.
S
olubilit
y Class

34.

43.
52.

35.

+ 36.

37.

44.

- 45.

+ 46.

53.

- 54.

+ 55.

62.

63.

64.

A
2

74.
Ethyl 75.
Alcohol

67.

68.

69.

76.

+ 77.

+ 78.

70.

71.

79.

80.

72.

73.

81.

82.

S
1

83.

Hexa
ne

84.

85.

86.

87.

88.

89.

- 90.

- 91.

92.

Phen

93.

95.

96.

97.

98.

99.

- 100.

- 101.

94.

ol
102. Tertbutyl
chloride
111. Tolu
ene

103.

104.

105.

106.

107.

108.

- 109.

- 110.

112.

113.

114.

115.

116.

117.

- 118.

- 119.

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120.

Sucr
ose

121.

122.

+ 123.

124.

125.

126.

127.

128.
2

129.Figure 1: Table of Results of Solubility Tests on the Compounds and their Structures
130.Source of Chemical Structures (images): http://www.chemspider.com/Chemical-Structure

III.

Conclusion

131.
Twelve different organic compounds solubility were tested to be able to
classify them into their respective solubility classes by using six solvents. These solvents
include water, ether, NaOH, HCl, NaHCO3, and concentrated H2SO4.
132.
Testing with water gives a quick idea of the polarity and the number of
carbons in the compound. The main rule that was followed to predict the solubility behaviour
of a compound is the like dissolve like rule, polar compounds are soluble/miscible in polar
solvents and non-polar in non-polar. Typically, only those with four carbons or lower are
soluble in water. Ether, only if soluble in water, distinguishes between inorganic salts and
organic compounds. Organic compounds are soluble in ether. If insoluble in water, using 5%
NaOH checks for the presence of any acidic functional groups, like those in carboxylic acids
and phenols. If soluble in 5% NaOH, 5%NaHCO3 essentially checks for how acidic the
compound is. Carboxylic acids are soluble here. If the compound is insoluble in 5% NaOH,
5% HCl checks for the presence of basic functional groups. Example of compounds soluble
in 5% HCl are amines. If the compound is still insoluble in 5% HCl and contains neither
Nitrogen nor Sulfur, concentrated H2SO4 is used to differentiate between carbonyl
compounds and purely hydrocarbon compounds.
133.
The results obtained showed that Hexane, Phenol, Tert-butyl and Toluene
are Inert Compounds; Benzyl Alcohol, and Benzaldehyde are Neutral Compounds;
Benzamide is a Miscellaneous Neutral Compound; Acetone and Ethyl alcohol are ether
soluble; Sucrose is ether insoluble; Benzoic acid is NaHCO 3 insoluble and Aniline is a basic
compound.
IV.

References

134.
McMurry, John. (2010). Foundations of Organic Chemistry Philippine Edition.
Quezon City, Philippines: C&E Publishing, Inc.
135.
Solomons, Graham, Fryhle, Craig B., Snyder, Scott A. (2014). Organic Chemistry
11E. 111 River Street, Hoboken: Wiley & Sons, Inc.
136.
Brown, Lemay, Bursten, Murphy, Woodward. (2012). Chemistry The Central
th
Science 12 Edition. Lake Ave., Glenview, IL: Pearson Education, Inc.
137.
University of Toronto Scarborough. (n.d.). Solubility Theory. Retrieved on
February 6, 2015, from http://webapps.utsc.utoronto.ca/chemistryonline/solubility.php

Page 5 of 5

138.
BioOrg.Chem By AJM. (n.d.). Classification of Organic Compounds by
Solubility. Retrieved on February 6, 2015, from
http://www.uobabylon.edu.iq/eprints/publication_10_5343_904.pdf
139.
Lionelha Macomber. (2011, February 27). Acetone. Retrieved on February 6,
2015, from http://chemistrymolecule.blogspot.com/2011/02/moleculechcl3.html
140.
141.
142.
143.
144.

145.

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