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Organic Derivatives of Water
Organic Derivatives of Water
Roque, Jason R.
Frias, Abigail Pauline F.
Bachelor of Science in Biology Major in Human Biology
College of Science
De La Salle University Dasmarias
Dasmarias, Cavite, Philippines
ABSTRACT
In this experiment the organic derivatives of water were tested. Based on the
characteristic solubility behavior and reactions we were able to distinguish the difference
among various organic derivatives of water. 95% ethanol, 2-butanol, tert-butanol, phenol,
diethyl ether, and three different unknown samples were placed on different test tubes
and were tested through solubility test in water, solubility test in NaOH, Bayers oxidation,
Chromic acid oxidation, Lucas test and Ferric chloride test. 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
all reactive except for solubility in water was the result of phenol. Diethyl ether was found
non-reactive in all the tests. At the end of the experiment the unknown samples were
identified as sample 1-alcohol, sample 2-ether and sample 3-aromatic alcohol/phenol
based on their solubility and reaction profile.
INTRODUCTION
Alcohols, Ethers, and Phenols are three different functional groups whose common denominator
is the presence of a singly bonded Oxygen atom in their chains. Alcohol is an organic compound in which
hydroxyl functional group (-OH). It is bound and connected to a carbon atom or hydrogen atom. The most
commonly used alcohol is ethanol, C2H5OH, with the ethane backbone. Alcohols are classified into
primary, secondary and tertiary, based upon the number of carbon atoms connected to the carbon atom
that bears the hydroxyl group. Namely, the primary alcohols have general formulas RCH2OH,secondary
ones are RR'CHOH they are both known to be reactive in various oxidizing agents while tertiary alcohols
are RR'R"COH, where R, R' and R" stand for alkyl groups. They are unreactive in oxidizing agents but
most reactive to nucleophilic substitution in Lucas reagent. Primary alcohols are found to be unreactive in
Lucas reagent while secondary alcohols are quite reactive. (2)
A compound which contains a six-membered aromatic ring, bonded directly to a hydroxyl group (OH) is called phenol. (4) Its structure is that of a hydroxyl group (-OH) bonded to a phenyl ring and it is an
aromatic compound. It is much acidic compared to alcohol and has limits in solubility in water. On the
other hand ethers are stable in bond that results to being generally unreactive. (1)(4) It has an oxygen
atom directly bound to two hydrocarbon (alkyl or aryl) groups and its common example is diethyl ether.
In this experiment we assume that those characteristics of alcohol, ether and phenol are to be
seen. The unknown samples will react to different tests for them to be classified and by then end of the
experiment correct identification will be achieved.
MATERIALS / REAGENTS & EXPERIMENTAL PROCEDURE
In performing the experiment, there are certain procedures in order to attain the right result. Place
5 drops/1mL of the different samples (1-butanol, 2-butanol, tert-butanol, phenol, diethyl ether, and the
other unknown samples) on different dry test tubes. Test the different samples into two kinds of test, the
solubility test, which is comprises of solubility in NaOH & water, and the other is chemical test, which is
comprises of Bayers oxidation test, chromic acid oxidation test, Lucas test, and Ferric chloride test. To
make it more detailed, for the solubility of water, add 5 drops/1mL of distilled water to each different
sample. Shake, and then observe the solubility. For solubility of NaOH, add 5 drops/1mL also to each
kind of sample. Shake also and observes it solubility. In order to determine the solubility of the mixture, for
fast reaction, there must be only single layer only, for slow, there will be a cloudy layer and for no
reaction, there is a presence of two layers. In the chemical test, for Bayers oxidation test, add 5
drops/1mL of the Bayers reagent to the samples. For the Chromic acid oxidation test, add 5 drops/1mL of
Na2Cr2O7 and 3 drops of concentrated H2SO4. For the Lucas test, add 10 drops of Lucas reagent and
observe it for a minimum of 5 minutes and maximum of 10 minutes. For the Ferric Chloride test, add ferric
chloride to the sample. Observe every reaction of the different samples.
Note: Phenol, concentrated sulfuric acid, sodium dichromate, and NaOH are corrosive
substances. Avoid direct skin contact. Di-ethyl ether vapor is toxic, avoid inhalation. (1)
DATA & RESULTS
In order to determine if the reaction of a compound is fast, slow or no change at all, there must be
a basis for every reaction. The table below shows the differentiation of solubility test, by having a single
layer, presence of emulsion or formation of two layers. Also, it shows the pertinent reaction of different
reagents according to its color or formation of cloudiness.
Table 1. Basis for Reaction (1)
SOLUBILITY
High Soluble / Miscible (++)
Slight Soluble / Miscible(+)
Insoluble / Immiscible (-)
Reagent
Color
Bayers Reagent
Chromic Acid
Dark Violet
Yellow Orange
Lucas Test
Ferric Chloride
Single Layer
Appearance Emulsion
Formation of Two Layers
CHEMICAL REACTIONS
Fast Reaction (//)
Slow Reaction
(+)
Fade & Brown
Fade & Brown
Precipitate
Precipitate
Change in Color
Change in Color
Cloudiness w/o
Cloudiness w/o
Shaking (Stand in
Shaking (Stand in
5 mins.)
10 mins.)
Black Violet /
Black Violet /
Black Greenish
Black Greenish
No Reaction
(-)
No Change
No Change
No Change
No Change
The table below shows the solubility and reactions of different 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 & Reaction Profile (1)
Solubility Test
Samples
H2O
NaOH
Ethanol
++
++
2-Butanol
+
tert-Butanol
++
Phenol
Diethyl Ether
Unknown 1
+
Unknown 2
Unknown 3
++
Legend: ++ = fast reaction / completely soluble
+ = slow reaction / slightly soluble
- = no reaction / insoluble
Identities of Unknown Samples
Sample 1: Primary Alcohol
Sample 2: Ether
Sample 3: Phenolic Compound
Bayers
Oxidation
++
++
+
++
++
Chemical Test
Chromic
Acid
Lucas Test
Oxidation
+
+
+
++
++
++
++
+
++
++
Ferric
Chloride
Test
++
++
I. Solubility Test
Solubility in Water (H2O): (5)
The different samples that are tested by solubility of water do not contain the same result. It is
concluded that there are factors that may occurred or inert to them that may or may not be applicable in
soluble in water.
- Basically, alcohols are insoluble in water except if they are in Carbon-6.
- Compound that is in a polar function group is more soluble.
e.g. butanol > butane
- The presence of polar functional group (-OH, -NH2, -CO2H)
- Like dissolve like.
- The more branching is present in a compound, the more it will be soluble.
e.g. tert-butanol > sec-butanol > n- butanol
- The branching or Carbon chain may also affect the solubility of the compound.
- The higher the number of Carbon atom, the more it is insoluble or less soluble.
Solubility in Sodium Hydroxide (NaOH): (6)
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. (6)
- 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.
Legaspi, G.A., Sta. Ana, S.T. Essentials of Organic Chemistry Laboratory. 2010
Retrieved on January 30, 2011. http://www.wikipedia.org/wiki/Alcohol
Retrieved on January 30, 2011. http://www.newencylopedia/Phenol
Retrieved on January 30, 2011. http://www.newencylopedia/Ethers
Retrieved on January 27, 2011. http://www.wikipedia.org/wiki/Solubility
Retrieved on January 27, 2011,
http://www.chemistry.ccsu.edu/glagovich/teaching/316/qualanal/solubility/naohs
(7) Retrieved on January 27, 2011, http://en.wikipedia.org/wiki/Chromic_acid
(8) Retrieved on January 27, 2011, http://www.enwikipedia.org/wiki/Lucas_reagent
(9) Retrieved on January 27, 2011, http://www.enwikipedia.org/wiki/Ferric_chloride_test/