ABSTRACT

In this experiment the organic derivati ves of water were tested. Based on
the characteristic solubility behavior and reactions, the difference among various organic
derivatives of water were able to be distinguished. Ethanol, 2-butanol, tert-butanol, phenol,
diethyl ether, and three diff erent unknown samples were placed on diff erent
test tubes and were tested through solubility test in water, solubility test in NaOH, Bayer’s
oxidation, Chromic acid oxidati on, Lucas test and Ferric chloride test. Through
certain indicati ons such as discolorati on and precipitati on, 1-Butanol was found to
be positive in all tests except with Lucas and Ferric chloride test. 2-Butanol was found to be
reactive except in solubility test in NaOH and Ferric chloride test while tert-butanol was
negative in all tests except with solubility test in water and Lucas test. On the other hand,
phenol was reactive to all except for solubility in water. Diethyl ether was found non-reacti ve
in all the tests. At the end of the experiment the unknown organic compound 3 was
identi fi ed as aromati c alcohol/phenol based on its solubility and reaction profile.

INTRODUCTION
Oxygen, along with hydrogen and carbon, is found in many important organic compounds. Alcohols,
Ethers, and Phenols are three different functional groups wherein all of them has the presence
of a singly bonded Oxygen atom in their chains. They are also known as organic derivatives of water for
they may be seen to arise from the replacement of one or both of the hydrogen atoms of water by an organic
group. In alcohols, one hydrogen is replaced by an aliphatic group, in phenols it is replaced by an aromatic group
and in ether, both hydrogen atoms are replaced.
Replacement shit
Alcohol is any compound with hydroxyl functional group (OH) attached to hydrocarbons.
It can be classified into three based on the number of carbon atoms connected to the carbon
atom that bears the hydroxyl group:
Primary Secondary Tertiary
Both primary and secondary alcohols are unreactive to nucleophilic substitution in Lucas
reagent, unlike tertiary alcohols.
In phenols, the hydroxyl group is directly bonded to an aromatic system. The aromatic ring makes
the hydroxyl group more acidic than it is in alcohols and has limits in solubility of water.
Ethers, on the other hand, are relatively inert molecules. It is unreactive for it is generally considered to
have stable bond.  
In this experiment, the difference among organic derivatives of water based on their
characteristic solubility behavior and reactions was aimed to be distinguished. Using this
knowledge, correct identification of unknown samples of alcohols, phenols, and ethers that
reacts with different tests can be done.
METHODOLOGY
In performing the experiment, there were certain procedures in order to attain the right
result. 5 drops of diff erent samples (1-butanol, 2-butanol, tert-butanol, phenol,
diethyl ether, and the other unknown samples) were placed on different dry test tubes. The
different samples were tested using the water solubility test, NaOH test, Bayer’s oxidation test,
chromic acid oxidation test, Lucas test, and Ferric chloride test. To test for the solubility in
water, 5 drops of disti lled water was dropped into each organic compounds. For
the solubility of NaOH, 5 drops of NaOH was added to each samples. Fo r
B a y e r ’ s   o x i d a ti o n t e s t , 5 drops of the Bayer’s reagent was added to the samples. For the
Chromic acid oxidation test, 5 drops of Na2Cr2O7 and 3 drops of concentrated H2SO4 was
added. For the Lucas test, 10 drops of Lucas reagent was added . Lastly, for the Ferric
Chloride test, 5 drops of ferric chloride was added to each samples. Each mixture was shaken
and every reaction of the different samples was observed.

RESULTS AND DISCUSSION

In order to determine if there is a reaction, there must be a basis for every reaction. The
table below shows the pertinent reaction of different reagents according to its color or
formation of cloudiness
Table 1. Basis for reaction
The table below shows the solubility and reacti ons of diff erent samples that
undergone into different test. This table shows the different derivatives of water and their
unique characteristics. Certain samples are shown and are the same with the other that shows
that they belong to same group.
Table 2. Solubility and reaction profile
I. Solubility in water
Based from the results of the experiment, there are factors that may have
occurred or inert to the compounds that may or may not be applicable in its solubility in water.
Alcohols are insoluble in water except if they are in Carbon-6. Compound that is in a polar
function group is more soluble. The presence of polar functional group (-OH, -NH2, -CO2H), the
branching or carbon chain present in a compound and the number of the carbon atom may also
affect the solubility of the compound.
II. Solubility in Sodium Hydroxide (NaOH)
The solubility of organic compound in NaOH is quite different in water. There are certain
characteristics that make other compounds soluble in it while insoluble in water. A compound
is deemed “soluble” in NaOH if it is significantly soluble in water. Some sodium salts  with highly
substituted Phenols are Insoluble in 5% NaOH.  Phenols react with sodium hydroxide solution to
give a colorless solution containing sodium phenoxide. Phenol dissolves in aqueous sodium
hydroxide because phenol behaves as an acid and gives up its proton to the hydroxide ion
which is a base. A soluble ionic product is formed. In this reacti on, the hydrogen ion
has been removed by the strongly basic hydroxide ion in the sodium hydroxide solution.
III. Bayer’s oxidation
Figure 1. Bayer’s oxidation reaction in Alkenes and Alkynes
Bayer's reagent is an alkaline solution of potassium permanganate, a powerful oxidant.
Reacti on with double or triple bonds (-C = C -   o r   - C ≡ C - )   i n   a n   o r g a n i c   m a t e r i a l
causes the color to fade from purplish-pink to brown due to a
p r e c i p i t a t e . T h e disappearance of the purple color and the appearance of a
brown precipitates concludes that it is a positive test. Often, the brown precipitate fails to
form and the solution turns reddish-brown. Easily oxidized compounds, aldehydes, formic acids
and its esters, and traced impurities present in alcohol give positive test. On the other hand,
carbonyl compound which decolorizes  bromine / carbon tetrachloride gives a
negative test.
IV. Chromic Acid Oxidation
Figure 2. Chromic Acid oxidation reaction
Chromic acid test is a test for oxidizables or any compounds that possess reducing
property. Chromic acid (acidifi ed dichromate, an oxidizing agent) can also be used to
distinguish between types of alcohols by oxidizing the alcohol. Primary alcohols are oxidized to
carboxylic acids, secondary alcohols are oxidized to ketones, while tertiary alcohols are not
oxidized.
V. Lucas Test
Figure 3. Lucas reaction
This test in alcohol differentiates tertiary alcohols from primary and secondary. It is
based on the difference in the reactivity of the three classes of alcohols with hydrogen halides.
When an alcohol is reacted with Lucas reagent (anhydrous ZnCl2, HCl), the resulting mixture
which is alkyl halide will not be soluble in water, thus presence of cloudiness, an
indicati on of positi ve test . With this reagent, time is essential in order to determine if the
compound reacts with it for it sometimes react longer than expected.
VI. Ferric Chloride Test
Figure 4. Ferric chloride reaction
This test is used to determine the presence or absence of phenols
in
a g i v e n s a m p l e . T h i s t e s ti s t r a d i ti o n a l   c a l o r i m e t r i c   t e s t   f o r   p h e n o l s   w h i c h   u s e
s   a   1 %   i r o n   ( I I I )   c h l o r i d e   s o l u ti o n   t h a t   h a s   b e e n n e u t r a l i z e d   w i t h   s o d i u m   h
y d r o x i d e   u n ti l   a   s l i g h t   p r e c i p i t a t e   o f   F e O ( O H )   i s   f o r m e d .   A   t r a n s i e n t   o r   pe
rmanent colorati on (usually purple, green or blue) indicates the presence
of a phenol or enol, which indicates a positive reaction also.
SUMMARY AND CONCLUSION

Alcohols, Ethers, and Phenols, also known as organic derivatives of water, are three
different functional groups wherein all of them has the presence of a singly bonded Oxygen
atom in their chains. In this experiment the organic derivati ves of water were tested
based on the characteristic solubility behavior and reactions. Ethanol, 2-butanol, tert-butanol,
phenol, diethyl ether, and three diff erent unknown samples
were placed on diff erent test tubes and were tested through solubility test in water,
solubility test in NaOH, Bayer’s oxidation, Chromic acid oxidati on, Lucas test and Ferric
chloride test.
Through certain indicati ons such as discolorati on and precipitati on, the
given organic compounds were classifi ed into what functi onal group they belong
to. A clear soluti on indicates solubility in water and NaOh which is a test for
alcohol, and ether. Phenol can also be positi ve when testi ng for NaOH solubility. A
brown precipitate inidicates positi ve result in Bayer’s oxidati on test, a test for the
presence of primary and secondary alcohols, as well as phenol. Chromic acid
oxidati on test, on the other is a test also for the presence of phenol, primary and
secondary alcohols, but a discolorati on into reddish or greenish mixture indicates
positi ve result. This discolorati on also indicates positi ve result in the Ferric
Chloride test. However, this test is only for the presence of phenol. Lastly, Lucas
test is a test for terti ary alcohol wherein a cloudy mixture indicates positi ve result.
From the data gathered, Ethanol was found to be positive in all tests except with
Lucas and Ferric chloride test. 2-Butanol was found to be reactive except in solubility test in
NaOH and Ferric chloride test while tert-butanol was negative in all tests except with solubility
test in water and Lucas test. On the other hand, phenol was reactive to all except for solubility
in water. Diethyl ether was found non-reacti ve in all the tests. At the end of the
experiment the unknown organic compound 3 was identi fi ed as aromati c
alcohol/phenol based on its solubility and reaction profile.

REFERENCES

Legaspi, G.A., Sta. Ana, S.T. Essentials of Organic Chemistry Laboratory. 2010
https://www.scribd.com/doc/48026330/Organic-Derivatives-of-Water
https://www.scribd.com/document/84066755/Organic-Derivatives-of-Water
https://www.scribd.com/doc/215489605/Exercise-7-Organic-Derivatives-of-Water