Organic Derivatives of Water

Alina May Aguilar

Diana Teresa Gatus
Ida Isabella Montesa
Aubrey Muriele Ramos
Brent Tenorio

De La Salle University-Dasmarias
Dasmarias City, Cavite, Philippines

ABSTRACT
Each type of alcohol has different reactivity towards various reagents. Primary and secondary
alcohols react with various oxidizing agents while tertiary alcohols are unreactive. This
experiment tested the organic derivatives of water. Five drops of ninety five percent ethanol, 2butanol, tert-butanol, phenol, and diethyl ether were prepared in separate test tubes. Each of
the samples were tested for the solubility in water, solubility in NaOH, Bayers oxidation,
Chromic acid oxidation, Lucas test and Ferric chloride rest. A few drops of water, NaOH,
Bayers reagent, Na2Cr2O7, Lucas reagent and Ferric chloride were added to each of the
samples in each test tube in different set ups.

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 that has a hydroxyl
functional group (-OH). It is bounded and connected to a carbon atom or hydrogen atom. Alcohols are classified
into primary, secondary and tertiary, based on the number of carbon atoms connected to the carbon atom that
bears the hydroxyl group. The primary alcohols have general formulas of RCH 2OH, secondary alcohols are
RRCHOH they are both known to be reactive in various oxidizing agents while tertiary alcohols are RRRCOH,
where R, R and R stand for alkyl groups. They are unreactive in oxidizing agents but most reactive to
nucleophilic substitution in Lucas reagent. The most commonly used alcohol is ethanol, C 2H5OH, with ethane as
the parent chain. Primary alcohols are found to be unreactive in Lucas reagent while secondary alcohols are quite
reactive.
A compound which contains a six-membered aromatic ring, bonded directly to a hydroxyl group (-OH) is
called phenol. 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 I water. On the other hand, ethers are
stable in bond that results to being generally unreactive. It has an oxygen atom directly bound to two hydrocarbon
(alkyl or aryl) groups and its common example is diethyl ether.

MATERIALS AND METHODS

Five drops of ninety five percent ethanol, 2-butanol, tert-butanol, phenol, and diethyl ether were placed in
separate dry test tubes and prepared for each of the tests. This experiment tested the solubility in water, solubility
in sodium hydroxide, Bayers test, Chromic acid oxidation, Lucas test and the Ferric chloride test. After each test,
their reactions were observed and classified as insoluble or non-reactive, slightly soluble or slow reaction and
soluble or fast reaction. The solubility test involved: solubility in water, five drops of distilled water was added to
each sample and observe, while in NaOH, five drops of NaOH was added to each of the samples and observed.
For the Bayers oxidation, five drops of Bayers reagent was added per sample, shook and the reaction was
observed. For Chromic acid oxidation, five drops of Na 2Cr2O7 and three drops of concentrated H 2SO4 were added
to each of the samples. The reaction was observed. For the Lucas test, ten drops of Lucas reagent was added
per sample shook and the reaction was observed for five to ten minutes. For the Ferric chloride test, five drops of
ferric chloride was added to each of the samples. The reaction was observed after shaking the solution.

RESULTS AND DISCUSSION

The table below shows the solubility and reactions of each sample that went the different tests. This table
shows the different derivatives of water and their unique characteristics.

Solubility Test
Samples
95 %
Ethanol
2-Butanol
TertButanol
Phenol
Diethyl
ether

Chemical Test
Chromi
c acid
Lucas
oxidati
Test
on

Solubility
in water

Solubilit
y in
NaOH

Bayers
oxidati
on

Ferric
Chlori
de Tes

++

++

++

++

++

++

++

++

++

++

Table 1 Results of Solubility and Chemical test

Table 1 shows that acetone, acetaldehyde and benzaldehyde are soluble in water; benzaldehyde and
cyclohexanone are soluble in sodium hydroxide; all have positive results in the 2,4-DNP test; acetaldehyde and
benzaldehyde have positive results in Tollens test; only acetone results positive in the Iodoform test while in the
Jones test benzaldehyde and cyclohexanone have positive results.

SOLUBILITY IN WATER:
The different samples that are tested by solubility of water do not contain the same result. It isconcluded
that there are factors that may occurred or inert to them that may or may not be applicable insoluble 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 NaOH:
The solubility of organic compound in NaOH is quite different in water. There are certaincharacteristics
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..

BAYERS TEST:
Bayer's reagent (KMnO4) is an alkaline solution of potassium permanganate, which is a powerful oxidant.
This reagent is used for oxidation (Bayers Oxidation). Reaction with double or triple bonds (-C=C- or -CC-) 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:

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.

LUCAS TEST:
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 reacted
with Lucas reagent (anhydrous ZnCl2, HCl), the resulting mixture which is an 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.
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, 2Methyl-2-Butanol).

FERRIC CHLORIDE TEST:

It is used to determine the presence or absence of phenols in a given sample. This test istraditional
calorimetric test for phenols which uses a 1% iron (III) chloride solution that hasbeenneutralized 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.

REFERENCES
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