Experiment 5:

Reactions of Aliphatic Alcohols and Phenol

Objective:
To investigate the reaction of aliphatic alcohols and phenols.

Chemicals:
Each of the chemicals in (i) to (v) required around 10ml
i
ii
iii
iv
v

Ethanol
Butanol
Butan-2-ol
2-methylpropan-2-ol
Phenol
Sodium carbonate solution
Sodium metal
Ethanoic acid/acetic acid
Concentrated H2SO4
Dilute H2SO4
Acidified potassium dichromate (K2Cr2O7)
Lucas reagent
Sodium hydroxide solution 2.0 M
Bromine water
Iron (III) chloride
Iodine solution
A bottle of disttiled water

Appratus:
10 test tubes, test tube rack, water bath, evaporating dish, stopper, wooden splints and
litmus paper or pH paper.

Results and data:

Observations
Test
Ethanol

Phenol

A) Solubility

A) Acidity
A) Addition

of

Na2CO3

The solution mixture became

The solution mixture form two

homogenous mixture.

layer.

The solution is acidic. It turns

The solution is acidic. It turns

litmus paper from blue to red.

litmus paper from blue to red.

2 drops of Na2CO3 turns litmus

2 drops of Na2CO3 turns litmus

paper from red to blue.

paper from red to blue.

A gas
B) Reaction

with

sodium metal

C) Esterification

Test
D)
i
ii
iii
iv
E)
i
ii
iii

2-ol
phenol
Lucas test
Butanol
Butan-2-ol
2-methylpropan-

A gas

was

produced

(white

smoke). It produced a pop sound

smoke). It produced a loud pop

when test with burning wooden

sound when test with burning

splint.

wooden splint.

Smooth or weak pungent smell

Smooth or weak pungent smell

was produced.

was produced.

i.
ii.

The solution turned from orange yellowish to dark brown

Two layers were formed. Top layer is cloudy brown and bottom

iii.
iv.

layer is light brown.

No changes occur. Only gas bubble were produced
The solution turn from black oily to dark brown with precipitate.

i.
ii.
iii.

The solution remains unchanged.

The solution turns from clear orange to milky solution.
The solution forms two layers. Top layer is clear and bottom

i.
on

methyl alcohols)
i Butanol
ii Butan-2-ol
iii 2-methylpropan-

The solution turns from cloudy white to clear white solution.

The reaction is very slow.

ii.

The solution turns from red precipitate to cloudy white. The

iii.

reaction is at normal rate.

The solution turns into clear yellow. The reaction is very fast.

on

the aromatic ring

Phenol
and
addition

of

bromine

water

drop.

(white

layer is cloudy yellow.

2-ol
F) Iodoform

2-ol
G) Substitution

produced

Observation

Oxidation
Ethanol
Butan-2-ol
2-methylpropan-

(reaction

was

i.

The solution turns into white solution. When bromine was

added, two layers were form. Top layer is cloudy while the
bottom layer is clear.

H) Test
group
Neutral

on
Fe

enol
(III)

chloride solution

The solution turns from colourless to dark blue.

into an aqueous
phenol

Questions/Discussions:
1. Select ONE compound from the following pairs of compounds which is more
water soluble. Explain your answer.
a) Ethanol and hexanol
Ans:
Ethanol is more soluble in water. Hexanol is not soluble in water. Ethanol consists of
two carbon atoms with a single bond between them. So it is easier for a short
hydrocarbon chain to bond with water molecules compared to hexanol which is a long
hydrocarbon chain.
b) Propanol and 1,2,3-propanetriol
Ans:

Propanol is more soluble in water. Propanol is an alcohol and polar, and exhibits
hydrogen bonding compared to 1,2,3-propanetriol. Water is polar and exhibits
hydrogen bonding. The polar natures of the alcohol and water allow the alcohol to be
completely miscible in water.
2. Suggest a chemical test(s) to distinguish the following pairs of compounds.
Include the reagents, reaction conditions and observations. Write the equation
involved.
a) 2-butanol and 3-pentanol
Ans:
To distinguish between 2-butanol and 3-pentanol, solubility test is needed. 2-butanol
is easier to bond with water molecule compared to 3-pentanol due to the short
hydrocarbon chain of 2-butanol.
Reagent: Sodium carbonate solution
Reaction condition: Room temperature
Observation: 2-butanol form homogenous mixture while 3-pentanol form 2 layer of
solution.
Equation: R-OH + Na R-O-Na+ + H2
b) Phenol and phenylethanol
Ans:
To distinguish between phenol and phenylethanol, esterification test is required.
Phenol does not form ester by direct reaction with carboxylic acid compared to
phenylethanol.
Reagent: Carboxylic acid
Reaction condition: Room temperature
Observation: Phenylethanol form ester directly from the reaction with carboxylic acid.
Equation: C6H5OH + R-COOH No reaction
c) Phenol and methylphenol
Ans:
To distinguish between phenol and methylphenol,iodoform test is needed.
Methylphenol react quickly with iodine compared to phenol.
Reagent: Iodine solution
Reaction condition: Room condition
Observation: Methylphenol when react with the reagent does not form precipitate.
Equation: CH3C6H4OH + 3I- CH3C6HI3OH + 3I
3. Explain the following observations.
a) Ethanol is less acidic than phenol.
Ans:
Phenol is more acidic than ethanol because of the presence of double bond in it.
Phenol can remove its hydrogen to make it more stable. Electron density on oxygen
atom decreases in comparison to oxygen atom present in alcohols, so phenol can
less donate than alcohol. According to Lewis concept of acid and base, which can
donate more is more basic and less is acidic.

b) Both phenol and methanol reacts with sodium but only phenol dissolves in
aqueous NaOH.
Ans:
The reason why phenol is more soluble in NaOH than in water is because phenol is
slightly acidic. By mixing with NaOH, it causes the phenol to release the H+ to form
sodium phenoxide. the reaction between NaOH and phenol is exothermic, and the
equilibrium lies far to the right. This makes the sodium phenoxide extra stable.
c) 2-methylpropanol does not give yellow precipitate with iodine in NaOH.
Ans:
A visible precipitate of this compound will form from a sample only when either a
methyl ketone, ethanal, ethanol, or a methyl secondary alcohol is present. 2methylpropanol is an primary alcohol, so it does not form precipitate.

d) 1-methylcyclopentanol does not change the purple colour of KMnO4/H+ ,

Ans:
KMnO4 is pink in a solution without oxidizing reagents. Adding ethanol should
change it to a brown solution. If adding ethanol can not change the solution to brown,
then its environment is already acidic and will not reduce.

Conclusion:
Hydroxyl group are connected to an alkyl carbon are called alcohols. They can be classified
into primary, secondary and tertiary alcohols depend on the number of carbon atoms bonded
to the carbon with the hydroxyl group. In hydroxyl group, they are alcohol and phenol. This
two compound can be distinguish by several tests such as oxdation, solubilty, esterification,
Lucas test, iodoform, substitution and test on enol group. Some test produced the same
product and reaction while some are not. In conclusion, the reaction of aliphatic alcohols and
phenol were investigated.

References:
1. John McMurry, Fundamentals of Organic Chemistry (5th Edition), 2003, pg. 106-126
2. G.L. Patrick, Organic Chemistry, (2nd Edition), 2004.