UNIVERSITI TEKNOLOGI MARA NEGERI SEMBILAN

KAMPUS KUALA PILAH

CHM207: ORGANIC CHEMISTRY

EXPERIMENT 5: REACTIONS OF ALIPHATIC ALCOHOLS AND PHENOL

GROUP MEMBERS:
1. NUR SABRINA BINTI MOHD SHAH (2022744707)
2. SITI AISHAH BINTI MUZAKKIR (2022318339)
3. ZUHAIRAH BINTI ISHAK (2022566501)

GROUP: AS1142A1
DATE: 13/12/2022
LECTURER NAME: DR ROPISAH ME
INTRODUCTION

Alcohol is an organic compound made of a saturated carbon and one or more hydroxyl groups.
Solubility of monohydroxyl alcohol gets worse when the relative molecular weight gets bigger.
Branched isomers are more soluble in water compared to unbranch isomers.. Alcohols undergo
oxidation, esterification, substitution, and elimination processes.
A hydroxyl group is immediately connected to a benzene ring in the molecule known as
phenol. The acidity of phenol is slightly lower compared to alcohol. As the number of hydroxyl
groups grows, so does its solubility. Electrophilic substitution dominates the phenol reaction.

OBJECTIVE

To investigate the reaction of aliphatic alcohols and phenols.

MATERIALS

Each of the chemicals in a-e required around 10 mL each

a) Ethanol
b) Butanol
c) Butan-2-ol
d) 2-methyl-propan-2-ol
e) Phenyl

Sodium carbonate solution

Sodium metal
Ethanoic acid
Concentrated H2SO4
Dilute H2SO4
Acidified potassium dichromate (K2Cr2O7)
Lucas reagent
Sodium Hydroxide solution, 2 M
Bromine water
Iron (III) Chloride
Iodine Solution
A bottle of distilled water

APPARATUS

10 test tubes
Test tube rack
Water bath
Evaporating dish
Stopper
Litmus paper or pH paper

PROCEDURES

(A) Solubility and acidity

1. In a test tube, 0.5 ml of ethanol and 2 ml of water were put. The solution became
homogeneous. This solution was tested with litmus paper or pH paper and then followed
by addition of sodium carbonate solution.
2. In a test tube, a small amount of phenol with water ( ~ 1g or 1 ml of phenol and 1 ml of
water) was heated. The solutions become homogeneous was observed. This solution
was tested with litmus paper or pH and then followed by addition of sodium carbonate
solution.

(C) Esterification
1. To a 2 ml of ethanol, 1 ml of ethanoic acid was added and then followed by addition of 2
ml of concentrated H2SO4. The mixture was shaken carefully and was heated for 5
minutes in a water bath. The mixture was removed from the water bath and left to cool
down, and then the mixture was poured in an evaporating dish containing about 5 ml of
sodium carbonate solution. The product smelled.

2. The reaction in C (1) was repeated on half a spatula of phenol.

(D) Oxidation
1. To a 1 ml of ethanol, 1 ml of dilute H2SO4 (to acidify the solution) was added and 0.5 of
K2Cr2O7 solution. A water bath was heated slowly because it was safer. The
observations were recorded.
2. The test of D(1) was repeated on:
(a) Butan-2-ol
(b) 2-methyl-propan-2-ol
(c) Phenol

(E) Lucas Test

1. 1 mL each of the following alcohols was taken:
a) Butanol
b) Butan-2-ol
c) 2-methyl-propan-2-ol

2. Each type of the alcohol was put in a separate test tube. In each tube, 3mL of Lucas
reagent was added at the same time. A stopper was put on each test tube, shaken and
was left to stand for a while. The results were observed and recorded down after 5
minutes.

(F) Iodoform (reaction on methyl alcohols)

1. 1 mL of butanol was added in a test tube and then followed by 4 mL of iodine solution. 2
M of sodium hydroxide solution was added drop by drop until the iodine color
disappeared.

2. The test in (F) was repeated with:

a) 2-butanol and
b) 2-methyl-2-propanol
DIAGRAM

(A) Solubility and acidity

1 mL of Phenol + 1 mL of water formed a two

layer solution

(C) Esterification

From right: ethanol and phenol

(D) Oxidation

From right: Phenol,

2-methyl-propan-2-ol,Butan-2-ol, Ethanol

(E) Lucas test

Credit to: “Lucas Test for Alcohols.” YouTube,

24 March 2021,
https://youtu.be/ZuAKxcxdDF8. Accessed 18
December 2022.

(F) Iodoform (reaction on methyl alcohols)

From right: butanol, 2-butanol,

2-methyl-2-propanol
 (G) Substitution on the aromatic ring

(H) Test on enol group

DISCUSSION

A) Solubility and Acidity

An ethanol solubility test revealed that the sodium mixture became homogeneous,
whereas a phenol solubility test revealed that the sodium mixture formed two layers.

Next, an ethanol acidity test shows that the solution is acidic because the litmus paper
shows a pH of 5, indicating an acidic environment, whereas a phenol acidity test shows that the
solution is acidic because the litmus paper shows a pH of 4, indicating an acidic environment.
Because the phenoxide ion is resonance stabilised, whereas neither the alcohol nor the
alkoxide ion is, we can say that phenol is more acidic than alcohol.

Finally, in an ethanol with Na2CO3 test, the solution is basic because litmus paper
showed pH 11, indicating a basic environment, whereas in a phenol with Na2CO3 test, the
solution is basic because litmus paper showed pH 9, indicating a basic environment.

C) Esterification
We put 1 ml of ethanoic acid into a 2 ml of ethanol then followed by addition of 2ml of
concentrated H2SO4. Shake the mixture and heat it for 5 minutes in the water bath. We poured
the mixture into a petri dish which contained 5 ml of sodium carbonate solution.The reason why
esters smell is mainly due to their weak intermolecular interactions. When we smelled the
ethanol, the smell was light and it remained colourless. When we smelled the phenol, it was
stinky and it turned colourless to emulsion. So, the experiments were accepted.

D) Oxidation

Aldehyde ethanal is created when ethanol is oxidised by sodium dichromate (K2Cr2O7)

and acidified in diluted sulfuric acid.

The colour change of the dichromate solution as it is reduced from the orange of Cr2O72−
to the green of chromium(III) ions (Cr3+) indicates the oxidation of the alcohol to an aldehyde. In
this reaction, two hydrogen atoms are removed from the ethanol to produce ethanal. Our
experiment failed because the solution turned into a blue solution.
 Secondary Alkanol Oxidation (secondary alcohol) Butan-2-ol (2-butanol) is a secondary
alkanol in which the OH functional group is attached to a carbon atom that is bonded to two
other carbon atoms:

The oxidation of a secondary alkanol (alcohol) produces an alkanone (ketone).

Butan-2-one (2-butanone or butanone) is produced by the oxidation of butan-2-ol (2-butanol) by
acidified dichromate solution, as shown in the equation below:

The reaction mixture should change colour from orange to green in the presence of
excess butan-2-ol (2-butanol) as the orange dichromate ions, Cr2O72-, are reduced to green
chromium(III) ions, Cr3+. Our experiment has two layers, with the top layer colourless and the
bottom layer blue, so our test failed.

2-methylpropan-2-ol (2-methyl-2-propanol) is a tertiary alkanol with an OH functional

group attached to a carbon atom that is bonded to 3 other carbon atoms:

The acidified dichromate solution will not react with 2-methylpropan-2-ol

(2-methyl-2-propanol). There will be no colour change because the orange dichromate ions will
not be reduced. The orange reaction mixture will remain orange. Our experiment has two layers:
a light green top layer and a dark green bottom layer, followed by a colourless solution.
 A conjugated diketone (benzoquinone) is produced when phenol is oxidised with
K2Cr2O7 in the presence of H (acid). When exposed to air, phenols gradually oxidise to
dark-colored mixtures containing quinones. Our experiment yielded a dark-brown precipitate
solution, indicating that our test was successful.

E) Lucas test

1-butanol, 2-butanol, and 2-methyl-2-propanol are treated sequentially with a solution of

ZnCl2 in concentrated aqueous HCl. The tertiary alcohol immediately forms a cloudy solution as
an SN1 reaction converts it to the water-insoluble alkyl chloride. The secondary alcohol,
2-butanol, is supposed to react after about 6.5 minutes, but we did not have enough time, so it
does not react during that time. The primary alcohol, 1-butanol, does not react.

F) Iodoform (reaction on methyl alcohols)

In reaction on methyl alcohols, we can see that the butanol changes from cloudy white
turns to black precipitate on the top and colourless at bottom. When we used 2-butanol, it turn
from red precipitate to 3 layers which was brownish on the top, colourless at middle and
yellowish precipitate at bottom. When we used 2-methyl-2-propanol, it changes from dark
brown to cloudy white. So, our experiment is accepted.

G) Substitution on the aromatic ring

When bromine water reacts with phenol solution, it decolorizes the bromine water and
forms a white precipitate with an antiseptic odour. 2,4,6-tribromophenol precipitates. Our
experiment consists of two layers in which the top layer is colourless (water) and the bottom
layer is orange (phenol solution). When bromine is added the top layer increases. So our
experiment failed.

H) Test to enol group

When we used aqueous solution and added 2 to 3 drops of neutral Fe (III) chloride
solution. Any colour change that we observed is colourless to brown precipitate on the bottom
and brown on top. So, our experiment was accepted.

CONCLUSION

Alcohols are hydroxyl groups that are linked to an alkyl carbon. Depending on the number of
carbon atoms bonded to the carbon with the hydroxyl group, they are classified as primary,
secondary, or tertiary alcohols. They are alcohol and phenol in the hydroxyl group. Several
tests, including oxidation, solubility, esterification, the Lucas test, iodoform, substitution, and the
test on the enol group, can distinguish these two compounds. Some tests yielded the same
product and reaction, while others did not. In conclusion, the reaction of aliphatic alcohols and
phenol was studied.

QUESTIONS

1. Select ONE compound from the following pairs of compounds which is more water
soluble. Explain your answer.

a) Ethanol and 1-hexanol

 - Ethanol is more water soluble because it has a short hydrocarbon chain
consisting of two carbon atoms with a single bond between them, make it
easier to bond with water molecules

b) 1-propanol and 1,2,3-propanetriol

- Because it is alcohol and has hydrogen bonding, 1-propanol is more

water soluble than 1,2,3-propanetriol. Alcohol is completely miscible in
water due to the polar nature of both the alcohol and the 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

- A solubility test is required to differentiate between 2-butanol and 3-pentanol. Because of
its shorter hydrocarbon chain, 2-butanol bonds more easily with water molecules than
3-pentanol.
- Reagent: Sodium carbonate solution
- Reaction condition: Room temperature
- Observations: 2-butanol from homogenous mixture while 3-pentanol form 2 layers of
solution.
- Equation: R-OH + Na = R-Na + ½ H2

b) Phenol and phenylethanol

- An esterification test is required to differentiate between phenol and phenylethanol. In
contrast to phenylethanol, phenol does not form esters through direct reaction with
carboxylic acid.
- Reagent: Carboxylic acid
- Reaction condition: Room temperature
- Observation: Phenylethanol forms ester directly from the reaction with carboxylic acid.
- Equation: C6H5OH + R-COOH = No Reaction

c) Phenol and Methylphenol

 - An iodoform test is required to differentiate between phenol and phenylethanol. In
comparison to phenol, methylphenol reacts rapidly with iodine.
- Reagent: Iodine solution
- Reaction condition: Room temperature
- Observation: Methylphenol when react with the reagent
- Equation: CH3C6H4OH + 3I = CH3C6HI3OH + 3I

3. Explain the following observations.

(a) Ethanol is less acidic than phenol.

- Because of the presence of a doubt bond, phenol is more acidic than ethanol. Phenol
can be made more stable by removing its hydrogen. Because the electron density on
oxygen atoms decreases when compared to oxygen atoms present in alcohols, phenol
can donate less than alcohol. According to Lewis' definition of acid and base, which can
donate more is more basic, and which can donate less is acidic.

(b) Both phenol and methanol react with sodium but only phenol dissolves in
aqueous NaOH.
- Because phenol is slightly acidic, it dissolves more readily in NaOH than in water. When
mixed with NaOH, the phenol releases the H+ to form sodium phenoxide. The reaction
of NaOH and phenol is exothermic, and the equilibrium is located far to the right. This
increases the stability of sodium phenoxide.

(c) 2-methylpropanol does not give yellow precipitate with iodine in NaOH.
- Only when a methyl ketone, ethanal, ethanol, or a methyl secondary alcohol is present in
a sample of this compound will it precipitate into a visible form. As a primary alcohol so
2-methylpropanol does not precipitate.

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

- In a solution without oxidizing agents, KMnO4 has a pink colour. It should turn into a
brown solution after adding ethanol. If adding ethanol does not make the solution turn
brown then the environment is already acidic and will not reduce.
REFERENCES

1. Prof. Steven Farme and Jim Clark, 2020. Acidity of Alcohols. Retrieved 2022, Dec 15,
from
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistr
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s_and_Phenols

2. “Difference Between Alcohol and Phenol in Tabular Form - BYJU'S.” Byju's,

Accessed date: 15 December 2022
https://byjus.com/chemistry/difference-between-alcohol-and-phenol/

3. “Chemical Reactions of Alcohols, Phenols and Ether: Videos and Examples.” Toppr,
Accessed date: 15 December 2022
https://www.toppr.com/guides/chemistry/alcohols-phenols-and-ethers/chemical-reactions
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https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Or
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