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 – Dasmariñas
Dasmariñas, 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, Bayer’s 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 Bayer’s 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 Bayer’s oxidation test, add 5
drops/1mL of the Bayer’s 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 (++) Single Layer
Slight Soluble / Miscible(+) Appearance Emulsion
Insoluble / Immiscible (-) Formation of Two Layers

CHEMICAL REACTIONS
Fast Reaction (//) Slow Reaction No Reaction
Reagent Color (+) (-)
Fade & Brown Fade & Brown
Bayer’s Reagent Dark Violet Precipitate Precipitate No Change
Chromic Acid Yellow Orange Change in Color Change in Color No Change
Cloudiness w/o Cloudiness w/o
Lucas’ Test Clear with Light Shaking (Stand in Shaking (Stand in No Change
Brown Tinge 5 mins.) 10 mins.)
Deep Yellow Black Violet / Black Violet /
Ferric Chloride Orange Black Greenish Black Greenish 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 Chemical Test

Chromic Ferric
Samples H2O NaOH Bayer’s Acid Lucas Test Chloride
Oxidation Oxidation Test
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

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.

Figure 1. Reaction of Phenol with Sodium Hydroxide

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 reaction, the
hydrogen ion has been removed by the strongly basic hydroxide ion in the sodium hydroxide solution.

II. Chemical Test

Bayer’s Oxidation:

Figure 2. Bayer’s Oxidation Reaction in Alkenes and Alkynes

Bayer's reagent (KMnO4) is an alkaline solution of potassium permanganate, which is a powerful
oxidant. This reagent is used for oxidation (Bayer’s Oxidation). Reaction with double or triple bonds (-
C=C- or -C≡C-) in an organic material causes the color to fade from purplish-pink to brown. The
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. Also, easily
oxidized gives a positive test.
- Positive test is done by most of aldehydes.
- Formic acid and its esters give also a positive test.
- Traced impurities that are present alcohol will then give a positive test.
- Carbonyl compound which decolorizes bromine / carbon tetrachloride will give a
negative test.

Chromic Acid Oxidation: (7)

Chromic acid is capable of many kinds of organic compounds. Chromic acid test, Di-chromate
test, and Jones test are the test for oxidizables or any compounds that possess reducing property (has an
alpha acidic hydrogen). Chromic acid (acidified 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; and tertiary alcohols are not oxidized.
 Figure 3. Chromic Acid Oxidation

Lucas Test: (8)

This test in alcohol will differentiate whether if it is primary, secondary, or tertiary alcohols. 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 and second layer will form if only the test is
positive. With this reagent, time is essential in order to determine if the compound reacts with it. In tertiary
alcohol it reacts immediately, for secondary alcohol, 3 – 10 mins. is needed, while in primary alcohol, it
may take an hour or longer or may even not react at all.

Figure 4. Lucas’ Test for Primary, Secondary and Tertiary Alcohol

Lucas’ test together with the samples will be considered positive reactions if they have these
following characteristics:

- No visible reaction (primary, such as normal amyl alcohol, 1-Pentanol)

- Solution turns cloudy in 3 5 mins (secondary, such as sec-amyl alcohol, 2-Pentanol)
- Solution turns cloudy immediately, and/or phase separate (tertiary, such as tert-amyl alcohol, 2-

Methyl-2-Butanol)

Ferric Chloride Test: (9)

It is used to determine the presence or absence of phenols in a given sample. This test is
traditional calorimetric test for phenols which uses a 1% iron (III) chloride solution that has been
neutralized with sodium hydroxide until a slight precipitate of FeO(OH) is formed. A transient or
permanent coloration (usually purple, green or blue) indicates the presence of a phenol or enol, which
indicates a positive reaction also.
 Figure 5. Ferric Chloride Test

REFERENCES

(1) Legaspi, G.A., Sta. Ana, S.T. Essentials of Organic Chemistry Laboratory. 2010
(2) Retrieved on January 30, 2011. http://www.wikipedia.org/wiki/Alcohol
(3) Retrieved on January 30, 2011. http://www.newencylopedia/Phenol
(4) Retrieved on January 30, 2011. http://www.newencylopedia/Ethers
(5) Retrieved on January 27, 2011. http://www.wikipedia.org/wiki/Solubility
(6) 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/