Organic Derivatives of Water

Abstract

Aside from carbon and hydrogen, oxygen can be found in a lot of

essential inorganic compounds and those classes containing this element can
be referred to as alcohol, phenol and ethers. In general they are collectively
known as the organic derivatives of water for they were from the replacement
of one or both of the hydrogen atoms of water by an organic group. In this
experiment, the students are to classify an unknown organic compound by
using and comparing the gathered data from the results of the known samples
which are ethanol, sec-butanol, tert-butanol, phenol and Diethyl ether in
various tests including solubility in water and NaOH, Bayer’s test, Chromic
Acid Oxidation test, Lucas test and Ferric chloride test. The assigned unknown
1 for the group was identified as a secondary alcohol for it has the same
reaction with sec-butanol.

Introduction

In Organic Chemistry, there are three functional groups that contain or

has the presence of Carbon and oxygen bond (C-O) namely alcohols, phenols
and ethers.

Alcohol has an OH group also known as the hydroxyl group that is

directly attached to a sp3 hybridized carbon. If it is attached in a sp2 then it is
called an enols. A common example of which is Ethanol and Methanol.
Moreover, alcohols can be categorized into three according to the attachment
of the hydroxyl group. For one, a primary alcohol means that the OH group is
attached to a primary carbon. When the attachment is at the secondary
carbon, it is called a secondary alcohol. Likewise, it is a tertiary alcohol if it is
on tertiary carbon. However, in general, those three types of alcohol differ in
reaction mechanisms.
 Phenol comprises an OH group or hydroxyl group attached to a benzene
ring. The molecular formula is usually C6H5OH and it is an example of special
aromatic compound also known as Hydroxy Benzene. Compared to other
aromatic compounds, phenol possess a higher boiling point which is 182oC.
Unlike alcohols, it is more acidic due to the presence of phenoxide anion. An
example of this functional group is Vitamin E and BHT that are considered as
radical inhibitors for they used the hydroxyl group (OH) to terminate radical
chain mechanism. However, a compound that contains more than one phenol
hydroxyl group is termed as polyphenol that has an ability to protect us from
many degenerative diseases.
Ether includes two R groups that are attached to oxygen which is also
classified into 2 types, symmetrical and unsymmetrical. If the substituents are
equal or have the same IUPAC name, then it is symmetrical, and it is identified
as unsymmetrical if they have different. The usual formula for ether is (ROR)
and the commonly used example is Diethyl ether which is a general
anesthetic. When they have oxygen enclosed in a cyclopropane, it is called an
epoxides.

One trait to be taken into consideration in order to identify an organic

compound is the reaction of the product when the reagent is mixed with an
organic sample. It can be determined by either a change of color, or a
formation of cloudiness or precipitates in the substance or the speed of the
reaction.

This experiment aims to distinguish the difference among various

organic derivatives of water based on their characteristic solubility behavior
and reactions. The gained knowledge was intended to help understand how to
identify unknown samples of alcohols, phenols, or ethers.

Methodology

In preparation for the laboratory experiment, 5 drops of ethanol, 2-

butanol, tert-butanol, phenol, diethyl ether and an unknown sample were
placed separately on a dry test tube. There were new set of sample for every
test that was performed. For the first test, it was intended to identify the
solubility of the samples in water. Five drops of distilled water was added into
the test tubes then shake for a few seconds and observed the solubility.
Likewise for the test of solubility of NaOH and Bayer’s oxidation, the only
difference with the procedure was the reagent used for each test but they
were of the same quantity which was 5 drops. NaOH was used for the
solubility test and Bayer’s reagent (KMnO4) for Bayer’s oxidation. Moreover,
in Chromic acid oxidation, 5 drops of Na2Cr2o7 was added into each samples
followed by 3 drops of concentrated H2SO4 then was observed. In Lucas test,
10 drops of the Lucas reagent was placed into the test tubes with samples
then was shake and observed for 5-10 minutes for the possible reaction.
Lastly, the Ferric chloride test was performed by adding 5 drops of Ferric
chloride and was then again shake and observed the reaction. After
performing all of the test for each samples provided, the students are to
classify the given unknown for each group based on the results of the known
samples.

Results and Discussion

Solubilit Solubility Bayer’s Chromic Lucas Ferric

y in H2O in NaOH test Acid test Chloride
Oxidation test
test
Ethanol + + + + - -
2- + + + + - -
butanol
Tert- + + - - + -
butanol
Phenol - + + + - +
Diethyl + + - - - -
ether
Unknown + + + + - -
1

Based from the table presented above, most of the organic samples
except for phenol had dissolved in water for it gave a clear solution which
means a positive result. Water being an inorganic compound, the classification
of alcohol is not the basis but the carbon chain length. Those substances
containing up to 4 carbons only with OH group would dissolve in water and
for those with exceeding number of carbons will not dissolve. An alcohol has
an OH group and it is polar, the alkyl group (R), is non polar. Since water is
polar, it will react with the OH group. “Like dissolves like”.

Moving on to the next column, the established results from the

experiment shows that all of the samples were soluble in NaOH that also
exhibits a clear solution. A compound is considered to be “soluble” in NaOH if
it is significantly soluble in water. However, in the case of phenol, it will still
react with NaOH giving a homogenous mixture which is usually sodium
phenoxide and water would be a byproduct. The reaction was due to the
strength of the basic hydroxide on the NaOH solution.

For Bayer’s oxidation test, a reagent was added which is known as

Potassium permanganate that is a strong oxidizing agent and it is often used
to oxidize unsaturated hydrocarbons leading to the formation of alcohols.
Only the primary and secondary alcohol as well as phenol would have a
positive reaction that was signified by a brown precipitate and it is similar to
the results that have yielded in the experiment. Primary alcohol when
introduced with KMnO4 will lead to the formation of carboxylic acid and it
will be ketone for secondary alcohol. The absence of the Hydrogen atom on
the carbon that contains the hydroxyl group is the reason behind the negative
reaction in tertiary alcohols.

Chromic Acid Oxidation is a test intended for any compounds that

possess reducing property. It can also be used in order to determine the type
of alcohol by oxidizing the alcohol. This test is similar with Bayer’s oxidation
as it only adhere to primary and secondary alcohol and phenols. However, the
positive result can be observed when there is a change in color and produces
either red or green precipitates.

The Lucas test which was second to the last to be performed is a test
that is usually used to classify what type of alcohol it is. Principally, tertiary
and secondary alcohol reacts often in this test and the primary alcohol does
not react with it. Between tertiary and secondary alcohol, it is the tertiary
which reacts faster to become a cloudy mixture compared to the other. The
reaction can be described as the substitution of Cl in the Hydrochloric acid
that generally replaces the OH group making it an alkyl halide as the major
product and having water as a minor one.

Lastly, the Ferric chloride test is used for the identification of the
presence of phenol within a compound. Definitely, only phenol reacted during
the experiment which has the same indication as the Chromic Acid Oxidation
test which was the change in color and producing dark green precipitates.

Grounded from the results gathered from the known samples and
comparing it to the remarks gained from the reaction of unknown, the group
classified it as part of the sec-butanol group that yields the same result.

Summary and Conclusion

The distinction of various organic derivatives of water varies based on

their characteristic solubility behaviour and reactions. There are various test
that would aid in classification and it is must to know every detail that would
lead to proper identification of samples. It is very critical for it is a choice
between having a positive or a negative results. Thus, accuracy and precision
with the amount of substance to be combined is necessary. Being
knowledgeable enough about how their structures look like based from their
names could be of great help in identifying them. However, when dealing with
the unknown, always remember that there is no 100% assurance that the
compounds are exactly the same but they have similar features that’s why
they are classified under that functional group.

As much as it is important to properly classify those organic

compounds, there are certain economical uses for each that everyone must be
aware of especially students in the field of science. Alcohols, phenol and ethers
are major ingredients of alcoholic beverages which according to studies have
some health benefits in our body. It can also use as alternative for fossil fuels
because it only produce carbon dioxide and water. Phenol is also a versatile
part to a large collection of drugs, like herbicides and pharmaceutical and is
also used as an oral anaesthetic/analgesic, and a general anaesthetic and
sedative in the medical field.
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