Organic Derivatives of Water

Joshua Joachim M. Pagaduan

Kae Peji

De La Salle University Dasmarinas
Dasmarinas City, Cavite, Philippines

Abstract
Organic Derivatives of Water (H
2
O) are alcohols, phenols and ether. Alcohol is an organic
compound that contains an OH group. Phenol has also the presence of an OH group attached
to a benzene ring and ether is an organic compound that has two alkyl groups attached to
oxygen. In this experiment various organic derivatives of water will be tested and their solubility
and chemical reactions will be tested and observed. These were the organic derivatives of water
that was been used during the experiment: Ethanol, 1-butanol, 2-butanol, tert - butanol, Phenol,
diethyl ether, Unknown Sample 1, 2 and 3. These nine organic compounds will be tested using
many test or reagents such as Bayers test (KMnO
4
), Lucas test, Ferric Chloride, Distilled H
2
O,
NaOH, and Chromic acid oxidation. Change in color or formation of precipitates are the
indicators of a positive reaction. After the experiment, it was concluded that Unknown Sample 1,
2 and 3 was alcohol, ether, and phenol respectively. Through this test, we will be able to
understand how alcohols, phenols, and ether differ from each other.


Introduction

There are three functional groups in Organic Chemistry that contain or has the presence of
Carbon and oxygen bond (C-O). These three functional groups are alcohol, phenol and ether.
Alcohol has an OH group or hydroxyl group that is directly attached to an sp
3
hybridized carbon.
If the hydroxyl group is attached to a sp
2
hybridized carbon then it is called an enols. Ethanol
and Methanol are common examples of this compound. Alcohols can be classified in 3 types
according to the attachment of the hydroxyl group. If the OH group is attached to a primary
carbon, then it is a primary alcohol. If the is attached to a secondary carbon, then it is a
secondary alcohol and if it is on tertiary carbon, it is a tertiary carbon. In general, primary,
secondary, and tertiary alcohols differ in reaction mechanisms. (1, 2)
Phenol contains an OH group or hydroxyl group attached to a benzene ring. Molecular
formula is usually C
6
H
5
OH. It is an example of special aromatic compound and it is also known
as Hydroxy Benzene (IUPAC Name). It has a distinct characteristic compared to other aromatic
compounds for it has higher boiling point which is 182
o
C. It is also distinct from alcohol for it is
more acidic due to the presence of phenoxide anion. Vitamin E and BHT are examples of
compounds that contain phenol. These compounds are considered as radical inhibitors for they
used the hydroxyl group (OH) to terminate radical chain mechanism. Polyphenol is a compound
that contains more than one phenol hydroxyl group. It is also known for its ability o protect us
from many degenerative diseases like cancer and Alzheimers disease. (2 , 3).
Ether has two R groups attached to oxygen. There are two types of ether, symmetrical and
unsymmetrical. If the substituents are equal or have the same IUPAC name, then it is
symmetrical, if the substituents have different IUPAC name then it is unsymmetrical. Ether
usually have the formula of (ROR). Epoxides are ethers that have oxygen enclosed in a
cyclopropane. Diethyl ether which is a general anesthetic is commonly used ether. (1, 2)


Materials and Methodology

Materials
95% Ethanol Unknown Sample 1 Lucas Reagent Test Tubes
1-Butanol Unknown Sample 2 1% Ferric Chloride Pasteur pipettes
2-Butanol Unknown Sample 3 Distilled water
Tert-Butanol Bayers Reagent 1.00 M NAOH
Phenol 1.00 M Na
2
Cr
2
O
7
Conc. H
2
SO
4

Diethyl Ether



Methodology








5 drops of the ff. on different test tubes





Solubility Solubility Bayers Chromic Lucas Test
In Water in NaOH Oxidation Acid Oxidation

+ 5 drops + 5 drops of + 5 drops, + 5 drops of + 10 drops
to each sample, NaOH. Shake Shake then Na
2
Cr
2
O
7.
Shake then
Shake then then observe observe the + 3 drops of observe
observe reaction Conc. H
2
SO
4
.
Observe the
reaction

FeCl
3
Test

+ 5 drops, Shake then
Observe.
Results and Discussion
Samples Solubility
in H
2
O
Solubility
in
NaOH
Bayers
Oxidation
Chromic
acid
Oxidation
Lucas
Test
FeCl
3
Ethanol ++ - ++ + - -
1-butanol ++ - ++ + - -
2-butanol ++ - ++ + ++ -
Tert butanol ++ - - - + -
Phenol - + - - - ++
Diethyl ether - - - - - -
Unknown 1 + - - ++ - -
Unknown 2 - - - - - -
Unknown 3 - + - + - ++
Ethanol, 1 Butanol, 2-Butanol, tert- butanol, phenol, diethyl ether, Unknown Sample 1,
2, and 3
++ (Fast Reaction), + (Slow reaction), - (No Reaction).

Identities of Unknown Sample
Sample 1: Alcohol
Sample 2: Ether
Sample 3: Phenol

Change in color of the reagents or formation of precipitates is a sign that the sample reacted
on it, the table below shows the signs of a positive reaction. Remember that time is also
essential, some compounds require amount of time to react on a reagent that is why we have a
slow reaction.
Reagents + Results
Water Homogenous Mixture
NaOH Homogenous Mixture
KMnO
4
Brown precipitate
Chromic acid oxidation Blue green precipitate
Lucas Test Cloudiness
FeCl
3
test Black, greenish, violet

Structures of Samples used



C H
3
OH
ethanol

CH
3
C H
3
CH
3
OH

Tert - butanol


O C H
3
CH
3

Butanol Diethyl ether
C H
3
OH
OH

2 Butanol Phenol

Solubility in H
2
O
Ethanol, 1-Butanol, 2-Butanol, and tert-butanol all dissolves in H
2
O giving us a homogenous
mixture. In water, the classification of alcohol is not the basis but the carbon chain length. A
maximum of 4 carbon containing the OH group will dissolve in water. Examples are Methanol,
Ethanol, propanol, and butanol, Pentanol, hexanol and other alcohols that have more that 4
carbon chain will no longer dissolve in water. 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. Rule of thumb is if the carbon chain length is increasing, the non polar part is increasing
making it impossible to dissolve in water. Unknown sample 1 is also soluble in water, thus it
may contain a short carbon chain. (4)

Solubility in NaOH
OH
NaOH
O
Na
+
O H
2

Reaction of phenol with NaOH

Phenol is the only organic compound that reacts with NaOH giving us a homogenous
mixture. Product of reaction is usually odium phenoxide and Water as a byproduct. Based on
the given reaction above, the H atom was removed and was replaced by Na. Removal of
hydrogen atom is due to the strength of the basic hydroxide on the NaOH solution. (3, 5)




C H
3
CH
3
OH

Bayers Oxidation (KMnO
4

C H
3
OH
ethanol
KMnO
4
C H
3
OH
O
C H
3
OH
KMnO
4
C H
3
OH
O
C H
3
CH
3
OH
KMnO
4
C H
3
CH
3
O

Reaction of alcohols with Bayers oxidation (Ethanol, Butanol, 2-Butanol)


Bayers oxidation or known as Potassium Permanganate is consist of K
+
and MnO
4
-
ions.
This is a strong oxidizing agent and it is often used to oxidize unsaturated hydrocarbons leading
to the formation of alcohols. Bayers oxidation can also oxidize alcohol; primary and secondary
alcohol will only react in this test. Primary alcohol (Ethanol and butanol) when introduced with
KMnO
4
will lead to the formation of carboxylic acid and Secondary alcohol will be ketone.
Tertiary alcohol will have no reaction in this test due to the absence of the Hydrogen atom on
the carbon that contains the hydroxyl group. As a result the formation of carbonyl group (C=O)
is not possible. In Primary and Secondary alcohol, there is the presence of Hydrogen to the
carbon that contains the OH group, thus making reaction possible. (6)

Chromic Acid Oxidation
Chromic acid test or also known as Jones reagent only works on Primary and Secondary
alcohols. This test is obtained by the addition of concentrated Sulfuric acid (H
2
SO
4
) to
dichromate. Products of this test are very similar to Bayers oxidation. Primary Alcohols are
synthesized to carboxylic acid and Secondary alcohols will be ketone. Secondary Alcohol will
react faster than primary alcohol in this test. After oxidation the Cr
+6
ion in the reagent was
reduced to Cr
+3
. This was the blue green precipitate that was seen in the reaction (7).


C H
3
OH
ethanol
C H
3
OH
O
C H
3
OH
C H
3
OH
O
C H
3
CH
3
OH
C H
3
CH
3
O
H
2
CrO
4
H
2
CrO
4
H
2
CrO
4

Reaction of Ethanol, Butanol, and 2-Butanol (respectively) on Chromic Acid Oxidation

Lucas Test

CH
3
C H
3
CH
3
OH
+
Cl H
ZnCl
2
CH
3
C H
3
CH
3
Cl
C H
3
CH
3
OH
+
Cl H
ZnCl
2
C H
3
CH
3
Cl
2-methylpropan-2-ol
butan-2-ol
+
O H
2
+
O H
2


Reaction of Tert - Butanol and 2- Butanol with Lucas Test

Lucas reagent is usually zinc chloride in a concentrated HCl. This test is usually to classify
primary, secondary and tertiary alcohol. Basically tertiary and secondary alcohol often reacts in
this test. Primary Alcohol will not react in this reagent. Tertiary alcohol will immediately turn into
a cloudy solution making it as a fast reaction while in secondary alcohol; it will take 3-5 minutes
for it to be cloudy. In this test, the reaction is substitution the Cl in the Hydrochloric acid
generally replaces the OH group making it an alkyl halide as the major product and Water (H
2
O)
as a minor product. (8)

FeCl
3
Test


Reaction of phenol with Ferric Chloride Test

FeCl
3
test or Ferric Chloride usually tests for the presence of phenol in a compound. In the
entire experiment only phenol reacted with FeCl
3
test giving us a black color which is a positive
reaction. Unknown sample 3 also reacted with this test which indicates that it is also a phenol.
(9)

Ether
Ether is usually not reactive because the C-O bond is hard to break, that is why it is often
used as a solvent. Unknown Sample 2 did not also react on all of the reagents which means
that it is also an ether. (10)

References:
(1) Legaspi, G. A. and Sta. Ana, S.T. Essentials of Organic Chemistry Laboratory. 2010.
Philippines.
(2) Smith J,G: Organic Chemistry: Second Edition: Mc-Graw Hill International
(3) Mccurry J, Simanck E: Fundamentals of Organic Chemistry: Sixth Edition: 2008; Thompson
Brooks/Cove
(4) Solubility of Alcohols: Retrieved 07 February 2014 from
www.chemwiki.vodavis/Organic_Chemistry/Alcohols/Properties_of_Alcohols.
(5) Phenol: Retrieved 07 February 2014 from
www.chemguide.co.uk/organicprops/phenol/other.html
(6) Bayers oxidation: Retrieved 07 February 2014 from www.ask.com/question/what-is-bayers
test for organic chemistry
(7) Jones reagent: Retrieved 07 February 2014 from www.organic-
chemistry.org/chemicals/oxidations/jones.reagent.shtm.
OH
FeCl
3
O
Fe
-
Cl
Cl
(8) Lucas Reagent: Retrieved 07 February 2014 from Wikipedia.org/Lucas reagent
(9 Eugenol reaction between, FeCl
3
and Bayers reagent: Retrived 4 December 2013 from
http://www.seattlecentral.edu/faculty/ptran/bastyr/summer%2007/organic%20lecture/Lab%20Pa
cketfall07.pdf
(10) Ether: Retrieved 08 February 2014 from
www.chemistry2.csudh.edu/rpendarvis/EtherSH.html.