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EXPERIMENT 3 : CHEMICAL PROPERTIES OF PHENOL

APPARATUS AND MATERIAL


Chemical: Phenol; sodium hydrogencarbonate; 2M sodium hydroxide solution; concentrated
hydrochloric acid; sodium, 1mm cubes; bromine water; iron(III) chloride solution, 0.5M; sodium
carbonate solution, 1M; universal indicator solution, ethanol, filter paper.
Apparatus: Safety spectacles; protective gloves; 6 test-tubes, with corks; test tube holder; washbottle of distilled water; 2 beakers, 250 cm 3; spatula; Bunsen burner, tripod, gauze and bench mat;
teat-pipette; thermometer 0-100oC; forceps.
INTRODUCTION
The purpose of this experiment is to see the effect of the benzene ring on the behaviour of the
hydroxyl group and vice versa.
The reactions you investigate are with the following reagents:
A.
B.
C.
D.
E.
F.

Water
Sodium hydrogencarbonate
Sodium hydroxide
Sodium
Bromine water
Neutral iron(III) chloride solution
HAZARD WARNING
Both phenol and bromine water attack the skin and give off irritating vapours. Therefore
you must:
WEAR GLOVES AND SAFETY SPECTACLES
AVOID CONTACT WITH SKIN
KEEP STOPPERS ON BOTTLES AS MUCH AS POSSIBLE.
Sodium is dangerously reactive. Therefore you must:
USE AS LITTLE AS POSSIBLE (1mm cube)
HANDLE WITH FORCEPS.
KEEP IT UNDER OIL
WEAR SAFETY SPECTACLES.

PROCEDURE
A. SOLUBILITY IN WATER
1.
pour about 5 cm3 of water into a test tube and add a heaped spatula-measure (about 1.5g) of
phenol. Cork and shake the tube. Note whether phenol dissolves in water.
2.
Add a further 3-4 measure of phenol, shake and note your observations.

3.

Place the test tube in a beaker of hot water for a few minutes, shake the tube and note your
observations.
4.
Allow the solution in the test tube to cool and note your observations.
5.
Add a few drops of universal indicator solution to the phenol-water mixture in one test tube
and distilled water in another.
B. REACTION WITH SODIUM HYDROGENCARBONATE
1.
Into a test tube pour about 1 cm3 of water and add 2-3 small crystals of phenol. Cork and
shake until the phenol has dissolved.
2.
Add about 0.5 g of sodium hydrogencarbonate and note your observation.
C. REACTION WITH SODIUM HYDROXIDE
1.
Pour about 5 cm3 of 2M sodium hydroxide into a test tube and add spatula measure of
phenol. Cork and shake the test tube.
2.
Add 3 more measures of phenol, cork and shake. Compare the solubility of phenol in water
from experiment A. Note your observations.
3.
Drop by drop, add 2 cm3 of concentrated hydrochloric acid. Shake the test tube and note
your observation.
D. REACTION WITH SODIUM
1.
In a fume cupboard, heat about 100 cm3 water in a beaker to about 60oC.
2.
Put a spatula measure of phenol in a dry test tube, and stand it in the hot water until the
phenol melts.
3.
Using forceps, pick up a 1 mm cube of sodium and remove the excess oil from its surface
on a piece of filter paper.
4.
Use a holder to remove the test tube from the hot water and, with the dry sodium into the
molten phenol.
5.
Apply a lighted splint to the mouth of the test tube.
E. REACTION WITH BROMINE WATER
1.
Into a test tube pour about 5 cm5 of water and add a spatula measure of phenol.
2.
Cork and shake until the phenol has dissolved.
3.
Pour half the solution into another test tube for reaction F.
4.
Add about six drops of bromine water to the aqueous phenol. Shaking the test tube after the
addition of each drop. Note your observations.
F. REACTION WITH NEUTRAL IRON(III) CHLORIDE SOLUTION
1. Into a test tube, pour about 1 cm3 of iron(III) chloride solution. Add sodium carbonate solution ,
drop-by-drop, until a trace of the brown precipitate just remains after shaking.
2. Add a few drop of this neutral iron(III) chloride solution to the phenol solution prepared in
reaction E. Note your observations.

3. Add a few drops of neutral iron (III) chloride solution to about 1 cm3 of ethanol. Note the
difference between ethanol and phenol in this test.
QUESTIONS
1. Which tests distinguish between ethanol and phenol?
2. Explain why phenol is more soluble in sodium hydroxide than in water?
3. Which tests indicate that phenol is a stronger acid than ethanol?
4. Which test indicates that phenol is a weaker acid than dilute mineral acid such ad HCl, H 2SO4
and HNO3 ?
5. How do you account for the fact that phenol decolourises bromine water and form a white
precipitate whereas ethanol does not?