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February 13, 2017



1. To observe the water solubility of alcohols relative to their chemical structures;
2. To determine the oxidation reactions of alcohols and phenols and their by-products; and
3. To distinguish primary, secondary and tertiary alcohols based on chemical characteristics.

Ethyl Alcohol Before agitation, 2 Blue green solution; aromatic
separate layers present. scent
After agitation, 1 layer
1-Butanol Before agitation, 2 Blue green solution with
separate layers present. separate layers (dark bottom
After agitation, 1 layer layer, translucent top layer);
present aromatic scent
2-Butanol Before agitation, 2 Blue green solution (two
separate layers present. separate layers present);
After agitation, 1 layer brownish orange precipitate
present present
2-Methyl-2- Before agitation, 2 Orange solution
propanol separate layers present.
After agitation, 1 layer
Cyclohexanol Two separate layers 3 layers present: top cerulean; Two layers formed;
present, even after middle blue green; bottom bottom purple color;
agitation brownish orange top yellow (FeCl3)

Phenol Black solution No purple color

Salicylic acid Before agitation, 2 Yellow color
solution separate layers present.
After agitation, 1 layer

Aqueous phenol + litmus paper Blue to purple
Phenol + litmus paper Blue to red
Ethanol + acetic acid + concentrated H2SO4 Fruity smell; clear solution
Ethyl alcohol Aldehyde ethanal
1-Butanol Butanal
2-Butanol 2-Butanone
2-Methyl-2-propanol No oxidation

Name the formula of second possible product formed from oxidation of ethyl alcohol:

In Part A of this exercise, the solubility of different alcohols in water was studied. Based
on Table 1, it was observed that all samples had separate layers. Although after agitating the
solution, the samples were homogenous, except for cyclohexanol. The general rule for solubility
is like dissolves like. That is, polar molecules are soluble or miscible in polar solvents, and
nonpolar molecules are soluble in nonpolar solvents. The hydroxyl group (-OH) is very polar, and
many alcohols are soluble in water, which in fact is very polar. Hydrocarbons are nonpolar and are
very insoluble/immiscible in water. Moreover, the general rule is increasing number of carbon
atoms, decreases its solubility in water. Cyclohexanol
For Part B (oxidation of alcohols), 1 mL of concentrated sulfuric acid was cautiously added
to 3 mL 5% sodium dichromate. This was the oxidizing agent utilized to test different alcohols and
its oxidation. Ethyl alcohol, 1-Butanol, 2-Butanol, Cyclohexanol exhibited a blue green solution.
With the exception of 2-Methyl-2-propanol and phenol, in which exhibited an orange solution and
black solution, respectively. Although the first four compounds mentioned differed in amount of
layers present and the intensity of color, it is evident that oxidation occurred due to the blue green
color. Using the oxidizing agent, Sodium dichromate, primary alcohols (alkanols), with the OH
functional group attached to a terminal carbon atom, were oxidized to aldehydes. This is signified
by the loss of hydrogen from the alkanol in order to produce a double bond to the oxygen.
Secondary alcohols, on the other hand, were oxidized to ketones. The oxidation is signified by the
loss of hydrogen from the alkanol in order to produce a double bond to the oxygen. Moreover, the
reaction mixture changed color from orange to blue green as the orange dichromate ions are
reduced to blue green chromium(III) ions. Lastly, tertiary alcohols (i.e. 2-Methyl-2-propanol)
cannot be oxidized using agents such as Sodium dichromate, since there was no reaction, the
oxidizing agent was not reduced, hence the color of the solution remained orange.
For ester formation, 4 drops of dilute acetic acid, 1 drop of concentrated sulfuric acid were
added to 10 drops of ethanol. Esters are produced when carboxylic acids are heated with alcohols
in the presence of an acid catalyst. The carboxylic acid is the acetic acid, alcohol is ethanol and
the acid catalyst used is sulfuric acid. Small esters, such as ethyl ethanoate, smell like typical
organic solvents. As esters get bigger, the smell may be similar to a fruit.
The last part of the exercise dealt with the Ferric Chloride test for Phenols. Phenols react
with FeCl3 to form a colored complex with the Fe3+ ion. The color varies from purple to orange
depending on the structure of the phenol tested. Alcohols do not form colored complexes with iron
ion. In this test, the appearance of a color is taken as a positive test and it indicates that a phenol
was present in the solution. However, as exhibited in Table 1, there was no purple color observed
in the solution. Hence, human error could be accountable for such discrepancy.

With the use of known compounds in different tests for alcohols and phenols, the objectives
were met. Most of the theoretical results for each test were congruent to the experimental results.
Qualitative analyses of the properties of alcohol and phenols were done with the help of the
following tests: (1) solubility test, (2) oxidation of alcohols, (3) ester formation and (4) ferric
chloride tests for phenols. Sources of error that affected series of tests were the possibility of
inaccurate measurements of reagents and contamination of the samples due to the mixing of
droppers and repetitive use of test tubes and Erlenmeyer flasks that were not washed well.

1. Explain why pentane is less soluble in water than isopropyl alcohol. Use drawings.
Pentane is a nonpolar compound whereas isopropyl is a polar compound. The general rule
of solubility is like dissolves like. As for isopropyl alcohol, the atoms of the OH group
form hydrogen bonds with the H and O atoms of water as illustrated below, thereby
allowing solubility.

2. Explain how glycerol behaves as it does in diethyl ether.

Each glycerol molecule has a three-carbon chain, with an OH group attached to each carbon
atom. The OH groups are responsible for making the compound highly soluble in water
and hygroscopic. It has only slight solubility in organic solvents, such as diethyl ether, and
it does not dissolve in hydrocarbons. Moreover, the ether oxygen can act as a hydrogen-
bond acceptor. The difference between the ether group and the alcohol group, however, is
that the alcohol group is both a hydrogen bond donor and acceptor. Hence, the alcohol is
able to form more energetically favorable interactions with the solvent compared to the
ether. With that said, alcohol is therefore more soluble.

3. Which of the compounds tested was the most polar? Draw its structure showing where
polarity originates in the molecule.
As previously mentioned, the general trend is that with increasing number of carbon
atoms, there is a decrease in solubility in water. Therefore, the most polar would be ethyl
alcohol it only has 2 carbon atoms.