nORGANIC CHEMISTRY FOR TECHNOLOGY

CHM 412
EXPERIMENT 4
REACTIONS OF ALIPHATIC ALCHOLS AND PHENOLS
NAME:

MARIAM HANANI ISMAIL

STUDENT ID:

2014827564

GROUP:

ED2604A

DATE OF EXPERIMENT:

5TH APRIL 2016

DATE OF SUBMISSON:

20TH APRIL 2016

INSTRUCTORS NAME:

MADAM FARIDAHANIM MOHD JAAFAR

EXPERIMENT 4
A.

REACTIONS OF ALIPHATIC ALCOHOLS

Apparatus
test tubes - 5
test tube rack- 1
water bath
evaporating dish -1
test tube stopper - 1
wooden splints -1
Chemicals
ethanol,
butanol,
butan-2-ol
2-methyl-propan-2-ol
sodium metal
glacial ethanoic acid/ethanoic acid
concentrated H2SO4
dilute H2SO4
Na2CO3(aq)
potassium dichromate (K2Cr2O7)
Lucas reagent.
Note: ethanoic acid=acetic acid

Pre lab assignment (11 marks)

1. Write a two paragraph theory on alcohols.
Alcohols are compounds in which one or more hydrogen atoms in an alkane have
been replaced by an -OH group. The structure of an alcohol is similar to water, a bent
shape. This shows the effect of electron repulsion. Like water, alcohols are polar,
containing an unsymmetrical distribution of charge between the oxygen and hydrogen
atoms. The high electronegativity of the oxygen compared to carbon leads to the
shortening and strengthening of the -OH bond. The presence of the -OH groups allows
for hydrogen bonding with other -OH groups, hydrogen atoms, and other molecules. The
boiling points are higher than those of their parent molecules.
Alcohols are able to undergo many chemical reactions. They
often deprotonation in the presence of a strong base. This weak acid behavior results in
the formation in an alkoxide salt and a water molecule. Hydroxyl groups alone are not
considered
good
leaving
groups.
Often,
their
participation
in
nucleophilic substitution reactions is instigated by the protonation of the oxygen atom,
leading to the formation a water moietya better leaving group. Alcohols can react with
carboxylic acids to form an ester, and they can be oxidized to aldehydes or carboxylic
acids.
2. Draw structures for ethanol, 2-butanol, 2-methyl-propan-2-ol.

Procedure
Experiment
a)
Reaction with sodium metal
A small amount (around half of a pea size)
of Na(s) was added to a test tube which
contains 1ml of ethanol. The test tube was
made sure it is dry before carrying out the
experiment. The test tube was closed with
a stopper. Presence of bubble was
observed and the gas was tested using a
burning wooden splint.

Observation:(1 mark)
Obtained:
Yellow solution was formed at the end of the
effervescence. The burning wooden splinter was
distinguished.
Expected:
The burning wooden splinter produced a pop sound.
Equation: (2 marks)
2CH3CH2OH(l)+2Na(s)2CH3CH2O(aq)+2Na+(aq)
+H2(g)

Conclusion: (1 mark)
Hydrogen gas was given off but the burning splinter
did not produce a pop sound. This may be caused
by the loose stopper that was used to contain the
hydrogen gas.
b) Esterification
2 ml of glacial ethanoic acid was added to
2 ml of ethanol, and then followed by
addition of 2 ml of concentrated H2SO4.
The mixture was carefully shaken and
heated for 5 minutes in a water bath. The
mixture was removed from the water bath
and left to cool, and then the mixture was
poured in an evaporating dish or a beaker
containing about 5ml of Na2CO3(aq). The
product was smelled.

Observation:(1 mark)
Colourless solution was formed and banana-like
smell was produced.
Equation: (2 marks)

Conclusion: (1mark)
Colourless ethyl ethanoate was produced giving a
sweet scent like a banana smell.
Experiment
c) Oxidation
1 ml of dilute H2SO4 and 0.5 ml of K2Cr2O7
solution was added to a 1 ml of ethanol,.
The mixture was heated slowly by using
the water bath. Observation was record

Observation:(2 marks)
Colour change:
The solution changes from orange to greenish blue.
Smell:

your (i.e. smell and colour change).

Balloon-like or banana-like smell was produced.

Structure of product:(2 marks)

d) Lucas test
1 ml of the following alcohols was added
in:
i) butanol,
ii) butan-2-ol
iii) 2-methyl-propan-2-ol

Conclusion: (1 mark)
The green colour indicates the presence of Cr3+ ion
and the balloon smell is the smell of the ethanoic
acid.
Observation(s):(3marks)
Butanol: light yellow solution was produced
Butan-2-ol: clear solution was produced
2-methyl-propan-2-ol: Cloudy milky solution was
produced.
Three equations required here:(6 marks)

In 3 separate test tubes. In each tube, 3 ml

of Lucas reagent was added at the same
time. A stopper was placed on each test
tube. The mixture was shaken and left it to
stand for a while. The results was observed
and recorded after 5 minutes.

Conclusions: (6 marks)
The Lucas reagent is used to categorize the
different types of alcohols based on the time taken
to form a turbid solution or precipitation. The
tertiary alcohol shows the fastest reaction followed
by secondary alcohol and primary alcohol forming
turbid solution.

B.

REACTIONS OF PHENOL

______________________________________________________________________
Pre lab assignment (7 marks)
1. Write a two paragraphs theory on phenol. (4 marks)
Phenol is a class of chemical compounds consisting of a hydroxyl group (
OH) bonded directly to an aromatic hydrocarbon group. They have unique properties and
are not classified as alcohols (since the hydroxyl group is not bonded to
a saturated carbon atom). They have higher acidities due to the aromatic ring's tight
coupling with the oxygen and a relatively loose bond between the oxygen and hydrogen.
The acidity of the hydroxyl group in phenols is commonly intermediate between that
of aliphaticalcohols and carboxylic acids (their pKa is usually between 10 and 12).
The chemical behavior of phenols is different in some respects from that of the
alcohols, so it is sensible to treat them as a similar but characteristically distinct group. A
corresponding difference in reactivity was observed in comparing aryl halides, such as
bromobenzene, with alkyl halides, such as butyl bromide and tert-butyl chloride. Thus,
nucleophilic substitution and elimination reactions were common for alkyl halides, but
rare with aryl halides. This distinction carries over when comparing alcohols and phenols,
so for all practical purposes substitution and/or elimination of the phenolic hydroxyl
group does not occur.
2. Draw the structure of phenol. (1 mark)

3. Arrange phenol, ethanol and benzoic acid in increasing acidity.(2 marks)

Ethanol, phenol and benzoic acid are the arrangement in increasing acidity.

Apparatus
test tubes- 5
test tube rack-1
blue litmus paper or pH paper

wooden splint- 1
Chemicals
Phenol
Na2CO3(aq)
Ether
Na(s)
bromine water
iron (III) chloride
sodium carbonate (Na2CO3(aq))
sodium bicarbonate (NaHCO3(aq))

Procedure
TRY TO USE SOLID PHENOL FOR BETTER OBSERVARTION AND RESULT
Experiment
a) Solubility and pH
Observations:
In a test tube, 1ml of phenol was heated
Room temperature:(1 mark)
with 1 ml of water in a water bath. This
Cloudy homogenous solution was formed.
solution was tested with a blue litmus
After heating: (1 mark)
paper. Then 1 ml of sodium carbonate
The solution changes from homogenous
solution was added in.
heterogeneous.
After addition of Na2CO3(aq): (1 mark)
Note: Observe whether the solution
Obtained:
becomes homogeneous at room
The solution changes from homogenous
temperature and after heating
heterogeneous.
Expected:
No changes.
Litmus paper or pH paper(1 mark)
Blue litmus paper changes to red.
Equation(s): (2 marks)
No reaction occurs.

to

to

Conclusion: (1 mark)
Phenol is a weak acid that does not react with
sodium carbonate (weak base). The obtained result
was different from expected due to the impurities
that present in the test tube. Phenol is soluble to
water.
b) About 1 ml of phenol was dissolved in Observations:(2 marks)
about 2ml of ether, and then a small piece The clear solution changes to yellow solution.
(around half size of a match stick) of Na (s) The burning wooden splint distinguished. Na metal
was added in. the gas was tested released shows effervesce.
with a burning wooden splint.
Equation: (2 marks)
No reaction.
Conclusion: (2 marks)
No reaction occur between ether and phenol but
CO2 gas present as the burning wooden splint
distinguished and Na give bubble.

Procedure
Experiment
c) Drop by drop an aqueous bromine
(bromine water) solution was added in an
aqueous phenol solution until a physical
change is observed.

Observations:(2 marks)
Early stage addition of bromine water:
The cloudy solution changes to oily clear solution.
Excess addition of bromine water:
Obtained:
Heterogeneous solution was formed. Clear solution
on top and oily brown solution on bottom.
Expected:
Bromine water will be decolourized and white
precipitate was formed with the smell of antiseptic.
Equation: (2 marks)

Conclusion: (2 mark)
The obtained result was different from expected
due to the insufficient amount of bromine water and
the impurities that present in the test tube.
d) 2-3 drops of neutral iron (III) chloride Observation:(1 mark)
solution were added into an aqueous Heterogeneous yellow solution was formed. Violet
phenol solution.
solution on top and dark blue solution on the
bottom.
No equation required:
Formation of complex
Conclusion: (1 mark)
The colour of the complex formed is intense violetblue solution.

Procedure
. Experiment
e) 1ml of phenol was added in 2 ml sodium
bicarbonate (NaHCO3) and the gas bubbles
or effervescences being released was
observes.

Observation:(1 mark)
Obtained:
Heterogeneous was formed. Clear solution on top
and oily yellow solution on bottom. Effervescences
were released.
Expected:
No changes.
Equation: (2 marks)
No reaction
Conclusion: (1 mark)
Phenol is a weak acid that does not react with
sodium bicarbonate (weak base). The obtained
result was different from expected due to the
impurities that present in the test tube.

Question:
1.

Name the gas that will be tested with the glowing wooden splint.
Oxygen gas is the gas that is tested with glowing wooden splint.

REFERENCES
1. Boundless. Alcohols. Boundless Chemistry. Boundless, 21 Jul. 2015. Retrieved 10 Apr. 2016
2.

from https://www.boundless.com/chemistry/textbooks/boundless-chemistry-textbook/organicchemistry-23/functional-group-names-properties-and-reactions-166/alcohols-638-7231/
Askiitians. Physical Chemistry. Retrieved 10 Apr. 2016 from

http://www.askiitians.com/forums/Physical-Chemistry/phenol-is-an-acid-but-does-notreact-with-sodium-b_80048.htm
3. Clark, J. 2016. The Acidity of Phenols. Retrieved 10 Apr. 2016 from
http://www.chemguide.co.uk/organicprops/phenol/acidity.html