Beruflich Dokumente
Kultur Dokumente
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.
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
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++
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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)
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.
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).
REFERENCES
(1) Legaspi, G. A. & Sta. Ana, S.T. 2010. Essentials of Organic Chemistry Laboratory
(2) Mcmurry J. Organic Chemistry 5th edition. 2000. Brooks/Cole Thomson Learning. United States of America
(3) Hill,G. & Holman J. 2000. Chemistry in Context, 4th Edition
(4) Retrieve on August 21, 2015: http://www.scribd.com/doc/48026330/Organic-Derivatives-of-Water#scribd
(5) Graham Solomons T.W., Frhyle C.B. 2008. Organic Chemistry 9th edition. John Wileyand Sons, Inc. United
States of America
(6) McMurry, J. Simanek, E. 2008. Fundamentals of Organic Chemistry 6th edition. Thomson Brooks/Cole. 5
Shenton Way #01-01 UIC Bldg. Singapore.