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Formal Report Exp 9
Formal Report Exp 9
Formal Report Exp 9
Hans Lorenzo Mercado, Dan Angelo Matias, Renai Matic, Celine Mindanao, Carmina Mislang
Group 6 2C Medical Technology Organic Chemistry Laboratory
ABSTRACT
Hydroxyl and Carbonyl containing samples were tested in this experiment. The samples were analyzed through tests
of alcohols in water, Lucas test, Chromic Acid test, 2,4-Dinitrophenylhydrazone (2,4-DNP) test,
Fehlings test, Tollens Silver Mirror test, and Iodoform test. Lucas test differentiates primary, secondary and tertiary
involving the solubility
alcohols. Chromic test was performed to know if the sample is oxidizable. 2,4-Dinitrophenylhydrazone test was
performed for aldehydes and ketones. Fehlings Test and Tollens Silver Mirror Test are tests for aldehydes. Iodoform
test is a test for methyl carbinol and methylcarbonyl groups. The samples are n-butyl alcohol, sec-butyl alcohol, tertbutyl alcohol, acetaldehyde, n-butylaldehyde, benzandehyde, acetone, and isopropyl alcohol.
INTRODUCTION
Hydroxyl group is used to describe the
functional group OH when it is a substituent in
an organic compound. [4] Representative organic
molecules containing a hydroxyl group are known
as alcohols. Hydroxyl groups are especially
important in biological chemistry because of their
tendency to form hydrogen bonds both as donor
and acceptor. This property is also related to their
ability to increase hydrophilicity and water
solubility [1].
There are three classifications of alcohols by
the carbon to which the hydroxyl group is
attached. Primary alcohols are those in which the
hydroxyl group is attached to the carbon with
only one carbon attached. Secondary alcohols are
compounds in which the OH- is attached to a
carbon which has two other carbons attached to
it. Tertiary alcohols are compounds in which a
hydroxyl group is attached to a carbon with three
attached carbons [3].
Carbonyl group is a family of functional groups
composed of a carbon atom double-bonded to an
oxygen atom: C=O. The group is a constituent of
carboxylic acids, esters, anhydrides, acylhalides,
amides, and quinones, and it is the characteristic
functional group of aldehydes and ketones [2].
Aldehydes are organic compound containing a
terminal carbony lgroup. This functional group,
called analdehyde group, consists of a carbon
atom bonded to a hydrogen atom with a single
covalent bond and an oxygen atom with a double
bond. Thus the chemical formula for an aldehyde
functional group is -CH=O, and the general
formula for analdehyde is R-CH=O.
EXPERIMENTAL
A. Compounds Used
The compounds used are n-butyl alcohol, secbutyl alcohol, tert-butyl alcohol, acetaldehyde, nbutylaldehyde, benzandehyde, acetone, and
isopropyl alcohol.
In this experiment, the materials needed are
Lucas reagent, chromic acid reagent, 95%
ethanol, Fehlings A and B, Tollens reagent, 5%
NaOCl solution, iodoform test reagent, 2,4dinitrophenylhydrazine, Pasteur pipette, test
tubes, beaker, and the sample compounds
ethanol, n-butyl alcohol, sec-butyl alcohol, tertbutyl alcohol, benzyl alcohol, n-butyraldehyde,
benzaldehyde, acetone, acetophenone, isopropyl
alcohol and acetaldehyde.
B. Procedure
1. Solubility of Alcohols in Water
Low molecular-weight amines and oxygencontaining compounds like alcohols, carboxylic
acids, aldehydes, and ketones are the only
soluble organic compounds in water.
In five different test tubes named as A to E,
place ten drops of ethanol, n-butyl alcohol, secbutyl alcohol, tert-butyl alcohol and benzyl
alcohol into the appropriate tube. Add 1 mL of
water to each of the test tubes and shake
thoroughly. If a cloudiness results, continue
adding 0.25 mL of water at a time, with vigorous
shaking, until a homogenous dispersion results. If
no cloudiness resulted after adding 2.0 mL of
water, the alcohol is soluble in water.
2. Lucas Test
To prepare the reagent for this test, dissolve 16
g of anhydrous zinc chloride in 10 mL of conc.
HCL. Allow the mixture to cool. After cooling, add
50 mg of the sample to 1 mL of reagent in a
small vial. Cap the vial and shake vigorously for a
few seconds. Allow the mixture to stand at room
temperature. Perform the test on n-butyl alcohol,
sec-butyl alcohol, tert-butyl alcoho, and benzyl
alcohol. Observe the rate of formation of the
cloudy suspension or the formation of two layers.
4. 2,4-Dinitrophenylhydrazone test
This test was performed on acetone,
acetaldehyde, n-butyraldehyde, benzaldehyde,
and acetophenone.
To prepare the reagent for this test, add a
solution of 3 g of 2,4-dinitrophenylhydrazine in
15 mL of conc. H2SO4 slowly, while stirring to a
mixture of 20 mL of water and 70 mL of 95%
ethanol. Stir and filter it. Place a drop of a liquid
sample into a small test tube. Add 5 drops of
95% ethanol and shake it well. Add 3 drops of
2,4-dinitrophenylhydrazine. If no yellow or
orange-red precipitate forms, allow the solution
to stand for at least 15 minutes.
5. Fehlings Test
This test was performed on acetaldehyde, nbutyraldehyde, acetone, benzaldehyde, and
acetophenone.
Fehlings reagent was prepared by mixing
equal amounts of Fehlings A and Fehlings B.
Fehlings A was prepared by dissolving 7 g of
hydrated copper (II) sulfate in 100 mL of water.
Fehlings B was prepared by mixing 35 g of
Potassium sodium tartrate and 10 g of Sodium
hydroxide in 100-ml water. 1-ml of freshly
prepared Fehlings reagent was placed into each
test tube. 3 drops of the sample to be tested
was added in to the tube. The tubes were then
placed in a beaker of boiling water and changes
within 10-15 minutes were observed.
7. Iodoform Test
This test was performed on acetaldehyde,
acetone, acetophenone, benzaldehyde, and
isopropyl alcohol.
2 drops of each sample was placed into its
own small vial or test tube. 20 drops of fresh
chlorine bleach (5% Sodium hypochlorite) was
slowly added while shaking to each test tube
and then, mixed. The formation of a yellow
participate was noted.
Ethanol
n-butyl
alcohol
secbutyl
alcohol
tertbutyl
alcohol
Benzyl
alcohol
Amount of
water (in
mL) needed
to produce
homogenous
dispersion
1 mL
2 mL
Solubility
in water
1.25 mL
miscible
1 mL
miscible
6.5 mL
immiscible
miscible
miscible
Results
Light
yellow
layer to light
green layer
Yellow layer to
light
green
layer
Yellow
green
layer
Orange layer
Orange to red
layer
Light
yellow
layer to light
green layer
n-butyl
alcohol
secbutyl
alcohol
tertbutyl
alcohol
Benzyl
alcohol
no
reaction
no
reaction
miscible
Cloudy
formation
immiscible
no
reaction
miscible
miscible
Substance
acetaldehyde
nbutyraldehyde
Benzaldehyde
acetone
Results
Orange ppt.
Orange ppt.
Orange ppt.
Orange ppt.
Results
Brick red ppt.
2 layer:
nbutyraldehyde
Benzaldehyde
acetone
green, brown
Brick red ppt.
3 layers:
Colorless, light
blue, royal blue
Blue solution
with orange ppt.
No change
Results
Silver
mirror;
black ppt.
gray solution
Clear solution
Gray solution
Results
Brown ppt.
Redish
briwn
ppt.
Yellow ppt.
Red solution
REFERENCES
[1] Bayguen, A.V., Cruz, C.T., de Guia,
R.M, Lampa, F.F., Pea, G.T., Sarile, A.S.
and Torres, P.C. (2009),Laboratory Manual in
Organic Chemistry,C&E Publishing, Inc.
[2] Carbonyl
http://en.wikipedia.org/wiki/Carbonyl
[3] Hydroxyl Group. (2010). In Encyclopdia
Britannica. Retrieved September 19, 2010, from
Encyclopdia
Britannica
Online:
http://www.daviddarling.info/encyclopedia
/P/phenol.html.
[4] Shriner, Fuson, Curtin. (1964). Systematic
Identification of Organic Compound: A Laboratory
Manual Fifth Edition. John Wiley & Sons, Inc. New
York: Van Hoffmann Press