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Abstract
Classification of Hydroxyl and Carbonyl containing compounds was done through different tests. The
samples were n-butyl alcohol, sec-butyl alcohol, tert-butyl alcohol, acetaldehyde, n-butyraldehyde,
benzaldehyde, acetone, acetophenone, and isopropyl alcohol. Each of the samples were tested through
solubility test of alcohols in water, Lucas test, Chromic acid test or the Jones oxidation test, 2,4Dinitrophenylhydrazone (2,4-DNP) test, Fehlings test, Tollens silver mirror test, and Iodoform test.
Solubility test of alcohols in water was used to determine the amount of water needed for it to produce a
homogenous dispersion and determine whether what kind of alcohol is soluble and insoluble in water.
Lucas test was used to differentiate primary, secondary, and tertiary alcohols. Chromic acid test was used
to determine if the sample is oxidized and can also be used to differentiate ketones from aldehydes. 2, 4Dinitrophenylhydrazone test was used to differentiate aldehydes and ketones. Fehlings test and Tollens
silver mirror test was used to determine whether the sample is an aldehyde. Lastly, Iodoform test was
used for classification of methyl ketones.
Introduction
Alcohols are organic compounds that may be
considered derivatives of water in which one of
the hydrogen atoms of water molecule (H-O-H)
has been replaced by an alkyl or substituted
alkyl group (Jaism& Mohammad, 2012).
Therefore, properties of alcohols may be related
to properties of both water and hydrocarbons
(Jaism& Mohammad, 2012). The alkyl group
could be primary, secondary, or tertiary, and may
be open chain or cyclic. Accordingly, alcohols
may be defined as organic compounds that
contain hydroxyl groups attached to alkyl,
substituted alkyl, or cyclic alkyl group
(Vollhardt,
2007).
Figure
1.
Structural
formula
of
Alcohol
http://media-cache-ec0.pinimg.com/736x/39/23/bd/3923bde41273f511199d81a9f0431a6a.jpg
Figure
2.
Classes
of
Alcohol
http://www.esu.edu/~scady/Experiments/Alcohols(summer).pdf
Figure
5.
Lucas
test
reaction
http://www.esu.edu/~scady/Experiments/Alcohols(summer).pdf
Figure
6.
Jones
oxidation
reaction
http://upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Jones
_Oxidation_Scheme.png/640px-Jones_Oxidation_Scheme.png
Figure
7.
2,4-DNP
test
reaction
http://www.esu.edu/~scady/Experiments/Alcohols(summer).pdf
Figure
9.
Iodoform
test
reaction
http://upload.wikimedia.org/wikipedia/commons/3/31
/Iodoform_test_alcohols.pn
Materials
Figure
8.
Fehlings
test
reaction
http://upload.wikimedia.org/wikipedia/commons/thumb/6/6
5/Fehling_orz.svg/1024px-Fehling_orz.svg.png
(2,4-DNP)
acetone,
acetaldehyde,
n-butyraldehyde,
benzaldehyde, and acetophenone. The results
were described.
E. Fehlings Test
Fehlings A was prepared by dissolving 7 g of
hydrated copper (II) sulfate in 100 mL of water,
while the Fehlings B was prepared by
dissolving 35 g of potassium sodium tartrate and
10 g of NaOH in 100 mL of water. One milliliter
of freshly prepared Fehlings reagent (made by
mixing equal amount of Fehlings A and
Fehlings B) was placed into each test tube.
Three drops was added to the sample that was
tested. The test tubes were placed in a beaker of
boiling water and the changes which occurred
within 10-15 minutes were observed. This test
was
performed
on
acetaldehyde,
nbutyraldehyde, acetone, benzaldehyde, and
acetophenone as well.
F. Tollens Silver Mirror Test
The reagent was prepared by adding 2 drops
of 5% sodium hydroxide solution to 2 mL of 5%
silver nitrate solution. Then only enough 2%
ammonium hydroxide was added to dissolve the
precipitate. No excess ammonia was added
because it will jeopardize the results. Four test
tubes with 1 mL of freshly prepared Tollens
reagent were prepared. Two drops each of the
sample was added separately: acetaldehyde,
benzaldehyde, acetone, n-butyraldehyde, and
acetophenone. It was allowed to stand for 10
minutes. In cases where there is no reaction
occurred, the test tubes were placed in a beaker
of warm water (30-50 C) for 5 minutes. The
observations were recorded.
G. Iodoform Test
Two drops of each sample (acetaldehyde,
acetone, acetophenone, benzaldehyde, and
isopropyl alcohol) was placed into its own vial.
Twenty drops of 10% KI solution was added.
Twenty drops of fresh chlorine bleach (5%
sodium hypochlorite) was added to each test
tube, and then mixed. Yellow precipitate
formation was noted.
Results and Discussion
Amount of water
(mL) needed to
produce a
homogenous
dispersion
1 mL
1.50 mL
Solubility
to water
Sec-butyl
alcohol
1 mL
soluble
tert butyl
alcohol
benzyl alcohol
1 mL
soluble
2 mL
insoluble
ethanol
n-butyl alcohol
soluble
soluble
Observed
colorless
slightly turbid
turbid
Observed
blue-green solution
blue-green solution
orange solution
blue-green solution
blue-green solution
orange solution
acetophenone
orange solution
Reaction observed
yellow ppt
yellow ppt
yellow ppt
yellow ppt
red-orange ppt
Reaction observed
brick-red ppt
brick-red ppt
brick-red ppt
blue solution
blue solution
Result observed
silver mirror
flesh solution
light yellow solution
with globules
dark-gray solution
turbid gray solution
Reaction observed
yellow ppt
no reaction
red ppt with globules
yellow ppt
yellow ppt
yellow crystal ppt
References
Clayden, J., & Bingham, M. J. (2008). Alcohols.
Stuttgart: Thieme.
Lehman, J. W. (2004). The student's lab
companion: laboratory techniques for organic
chemistry. Upper Saddle River, N.J.: PrenticeHall.
Jaism, A. M., & Mohammad, D. H.,
(2012). Practical Organic Chemistry. 1st ed.
Baghdad: Baghdad University Publishing.
Jones, M. (2000). Organic chemistry (2nd ed.).
New York: W.W. Norton.
Jones, M., & Gingrich, H. L. (2005). Study
guide/solutions manual for Jones's Organic
Chemistry (3rd ed.). New York: W.W. Norton.
Mariappan, M. (2009). Organic Chemistry Lab
Manual. Dubuque, IA: Kendall Hunt.
Martin, S. F., & Gilbert, J. C. (2011). Organic
Chemistry Lab Experiments: Miniscale and
Microscale (5th ed., Int'l ed.). Boston, MA.:
Brooks/Cole, Cengage Learning.
Pellegrini, F. (2000). Organic chemistry II.
Foster City, CA: IDG Books Worldwide.
Simek, J. W., & Wade, L. G. (2003). Organic
Chemistry: Solutions Manual (5th ed.). New
York: Prentice Hall.
Sinton, M. (2009). Organic chemistry. Dubuque,
Iowa: Kendall Hunt Pub. Co..
Tojo, G., & Fernandez, M. (2006). Oxidation of
alcohols to aldehydes and ketones: a guide to
current common practice. New York, NY:
Springer.
Vollhardt, K. C., & Neil E. S., (2007). Organic
Chemistry. 5th ed. New York: W.H. Freeman.
Appendix
http://upload.wikimedia.org/wikipedia/
commons/thumb/d/d4/Ethanol2.svg/12
80px-Ethanol2.svg.png
Ethanol
http://www.esu.edu/~scady/Experiments/Alcoho
ls(summer).pdf
Schematic diagram of the
differentiating tests
http://upload.wikimedia.org/wikipedia/
commons/thumb/e/e6/2Butanol_Structural_Formula_V.1.svg/12
80px-2Butanol_Structural_Formula_V.1.svg.pn
g
Sec-butyl alcohol
http://upload.wikimedia.org/wikipedia/
commons/thumb/5/53/Butan-1ol_Skelett.svg/1280px-Butan-1ol_Skelett.svg.png
n-butyl alcohol
http://upload.wikimedia.org/wikipedia/
commons/thumb/4/4a/TertButanol_Structural_Formula_V.1.svg/78
5px-TertButanol_Structural_Formula_V.1.svg.pn
g
Tert-butyl alcohol
Acetone
htt
p://upload.wikimedia.org/wikipedia/co
mmons/5/5a/Benzyl-alcohol-2Dskeletal.png
Benzyl alcohol
http://upload.wikimedia.org/wikipedia/
commons/thumb/8/88/Acetophenone_
200.svg/1280pxAcetophenone_200.svg.png
Acetophenone
http://upload.wikimedia.org/wikipedia/
commons/thumb/1/1c/Butyraldehyde_
200.svg/1280pxButyraldehyde_200.svg.png
n-butyraldehyde
http://upload.wikimedia.org/wikipedia/
commons/thumb/5/57/2Propanol2.svg/1280px-2Propanol2.svg.png
Isopropyl alcohol
http://upload.wikimedia.org/wikipedia/
commons/thumb/2/21/Aceton.svg/128
0px-Aceton.svg.png
http://upload.wikimedia.org/wikipedia/
commons/thumb/4/47/Acetaldehyde_2
00.svg/1280pxAcetaldehyde_200.svg.png
Acetaldehyde