Alcohol and Phenols

Introduction

Alcohols are hydrocarbon derivatives in which one or more hydrogen atoms have been replaced
by the hydroxyl or OH group. Their general formula are is R-OH. They are classified in two ways
according to the position of the carbon atom to which the OH group is attached. Alcohols that
contain one OH group are monohydric alcohols. Those containing two OH groups are called
dihydric alcohols and those containing three OH groups, trihydric alcohols. Polyhydric alcohols
are alcohols having more than one OH group. Primary alcohols are alcohols in which the OH group
is attached to a primary or end carbon. Secondary alcohols in which the OH group is attached to a
secondary carbon, a carbon which is attached to two other carbon atoms in tertiary alcohols, the
OH group is attached to a tertiary carbon, which is carbon is attached to three other carbon atoms.
Properties of alcohols. Alcohols are soluble in water. This is due to the hydroxyl group in
the alcohol which is able to form hydrogen bonds with water molecules. Alcohols with a smaller
hydrocarbon chain are very soluble. Phenols are more acidic than alcohols because of the tendency
of a lone pair of electron of oxygen to interact with the pi electrons of the benzene ring. The
delocalization results in a positive charge on the oxygen-hydrogen bond. Phenols generally have
higher boiling points in comparison to other hydrocarbons with equal molecular masses. The main
reason behind this is the presence of intermolecular hydrogen bonding between hydroxyl groups of
phenol molecules. In general, the boiling point of phenols increases with increase in the number of
carbon atoms. The hydroxyl group determines the solubility of phenol in water. The hydroxyl group
in phenol is responsible for the formation of intermolecular hydrogen bonding. Thus, hydrogen bonds
form between water and phenol molecules which make phenol soluble in water.

The experiment was conducted with the following: First is to determine the reaction of alcohols and to
observe the oxidation of alcohols with Chromic Acid and Potassium Permanganate; Second is to
distinguish the acidity of Alcohols and Phenols; lastly to determine the properties of phenols with ferric
chloride and the esterification with glacial acetic acid and ethanol.
Methodology

A. Material and Apparatus

The chemicals used in the experiment are as follows: Ethanol alcohol, Isopropyl alcohol,
tert-butyl alcohol, n-butyl, Benzyl alcohol, Phenol, Resorcinol, Salicylic acid, Potassium
dichromate, Sulfuric acid, Potassium permanganate, anhydrous zinc chloride,
Hydrochloric acid, Ferric chloride, and Glacial acetic acid.

The apparatus used include beaker, iron stand, iron ring, alcohol lamp, test tube, test tube
rack, wire gauze, Litmus paper and tong.

B. Procedure

A. Physical Properties of Alcohol

The following are used ethyl alcohol, isopropyl alcohol, tert-butyl alcohol, n-butyl alcohol
and benzyl alcohol.

a. Solubility in Water
The 5 test tubes are labelled with the name of the alcohols. A half dropperful of
labelled alcohol and 2 mL water was added to each test tube. Each test tube was
shake. It was accounted for the decrease in the solubility of the alcohols as the
carbon chain increases or as the number of branched carbon atoms increases.
b. Combustion
We ignited a match over one mL of 95% ethyl alcohol in a watch glass. It was
observed and recorded the color and sootiness of the result of the flame. It was done
the same with 45% ethyl alcohol.

B. Chemical Properties of Alcohols

Reaction which involves Displacement of H of OH

 1. Acidity of alcohols and Phenols

A pH paper was moisten with pure ethyl alcohol. The pH was noted. Another piece of
pH paper was used with pure phenol and the pH was recorded. The relative acidity of
the two compounds were recorded.

2. Oxidation of Alcohols

a) Reaction with Chromic Acid

A 1mL of ethyl alcohol, isopropyl alcohol, and tert-butyl were put in three separate test
tubes. 5 drops of potassium dichromate and 5 of 6N h2SO4 and warmed. The color and
odor of the solution were noted. The ease by which of the alcohols was

oxidized were compared. The equations for the reactions involved in each were written.

b) Reaction with Permanganate

A 1 mL of H2SO4 was added to 2mL of each sample. A few crystals of KMnO4

down the test tube was draw. The flashes on the boundary of the two layers were noted.
Do not hold the test tube. Let it stand.

Reaction which involves displacement of OH

1. Reaction with Lucas Reagent

1 mL of ethyl alcohol, isopropyl alcohol, and tert-butyl alcohol in three separated
test tubes were transferred. 2 mL of Lucas reagent (anhydrous zinc chloride in
concentrated hydrochloric acid) was added to each test tubes. It was shaken well.
Let them stand. Time required for the formation of an insoluble layer of emulsion
was noted.

C. Properties of Phenol

1. Ferric chloride Test

 1 mL of phenol, resorcinol, salicylic acid, and ethyl alcohol in four separates test
tubes were placed. A 1 drop of freshly prepared ferric chloride solution. The color
obtained was observed.

D. Esterification with glacial Acetic Acid

1. Glacial Acetic Acid

1 mL of ethyl alcohol in a dry test tube was placed. 1 mL glacial acetic acid and 2
drops concentrated H2SO4 was added. The odor of the mixture was carefully noted
then it was placed in a hot water bath for a couple of minutes.

Results:

Solubility in Water

Sample Observation
Ethyl Alcohol Soluble
Isopropyl Alcohol Soluble
Tert-butyl Alcohol Soluble
n-butyl Alcohol Slightly soluble
Phenol Moderately soluble
Benzyl Alcohol Slightly Soluble

Combustion

Observation Observation
Color of the Flame Soot
95% ethanol Blue flame Without soot
45% ethanol Yellow flame With soot
Acidity of Alcohols and Phenols

Sample pH
Ethanol 6- less acidic
Phenol 5- more acidic

Oxidation with Chromic Acid

Sample Observation Reagents

Ethanol Green solution/ precipitate Potassium dichromate,
Sulfuric acid
Isopropyl Alcohol Green solution/ precipitate Potassium dichromate,
Sulfuric acid
Tert-butyl Alcohol No visible result (yellow Potassium dichromate,
solution) Sulfuric acid

Oxidation with Potassium Permanganate

Sample Observation Reagents

Ethanol Brown precipitate Potassium Permanganate &

Sulfuric Acid
Isopropyl Alcohol Brown precipitate Potassium Permanganate &
Sulfuric Acid
Tert-butyl Alcohol No visible result Potassium Permanganate &
Sulfuric Acid

Formation of Alkyl halide by Lucas Reagent

Sample Observation Reagents

Ethanol Layers forms after 10mins. Anhydrous Zinc Chloride &
Hydrochloric Acid
 Isopropyl Alcohol Layers forms within 5mins. Anhydrous Zinc Chloride &
Hydrochloric Acid
Tert-butyl Alcohol Layers forms immediately Anhydrous Zinc Chloride &
Hydrochloric Acid

Ferric Chloride Test

Sample Structure Observation Reagents

Ethanol Ch3Ch2Oh No visible Ferric Chloride
result(Yellow
solution)
Phenol Violet complex/purple Ferric Chloride
precipitate
Resorcinol Violet complex/purple Ferric Chloride
precipitate

Salicylic Acid Violet complex/ Ferric Chloride

purple precipitate

Esterification with Glacial Acetic Acid

Sample Reagent Odor

Ethyl Alcohol CH3COOH Glacial acetic Sweet-smelling/fruity odor
Acid

Discussion

Alcohols and Phenols experiment aim to determine the Physical properties of alcohols including
its solubility and combustion. Also the chemical reactions which also includes the acidity of each
compounds, oxidation of alcohols using Potassium permanganate, Chromic acid, and Lucas
Reagent. We also identify the properties of phenols using ferric chloride test, and reaction of
alcohol when interacted with a carboxylic group, using glacial acetic acid and ethanol.
Physical Properties of Alcohols

Water Solubility

The general rule in solubility is “like dissolves like.” Since the OH group makes alcohols polar,
they will mix with polar solvents. Ethyl alcohol, Isopropyl alcohol, and Tert-butyl are more
soluble. Compared to n-butyl, Phenol, and Benzyl alcohol. For a reason that Ethyl alcohol,
Isopropyl alcohol, and Tert-butyl alcohol are more lighter in molecular weight than than n-butyl,
Phenol, and Benzyl alcohol, because as the molecular weight increases the solubility decreases.
Branched isomers are more soluble which is the tert-butyl and unbranched isomers which is the n-
butyl.

Combustion

Ethanol is a chemical compound made up of carbon, hydrogen and oxygen atoms. When ethanol is burnt,
it reacts with oxygen and produces water and carbon dioxide. We used 95% ethanol alcohol and 45%
ethanol alcohol and we ignited it with a match to test its flammability. The 95% ethanol alcohol produces
a blue flame, a non-luminous flame and it do not have a soot. Which means it is a complete combustion
due to the high ethanol alcohol percentage it contains than water which is only 5%. The 45% ethanol alcohol
produces a yellow flame, a luminous flame and it produces a soot which means it is an incomplete
combustion due to the low ethanol alcohol percentage it contains. Complete combustion happens when a
solution contains more ethanol alcohol and incomplete combustion happen when there is more water than
ethanol alcohol. With a chemical formula:

95% ethanol alcohol

2CH3cH2cH3OH + 5O2 → 2CO2 + 6H2O (complete combustion)

45% ethanol alcohol

2CH3CH2OH + 3O2 → CO2 + 6H2O + C (incomplete combustion)

Chemical Properties of Alcohols

Acidity of Alcohols and Phenols
Phenols are more acidic compare to ethanol because phenols can lose hydrogen ion due to the
phenoxide ion formed is stabilized to some extent. The negative charge on the oxygen atom is
delocalized around the ring. The more stable the ions is, the more likely it is to form. Also one of
the lone pairs on the oxygen atom overlaps with the delocalized electron on the benzene ring.
When a pH paper was moisten with pure ethanol it does not show positive reaction the pH paper
remained blue, but when a pH paper was moisten with pure phenol it reacted, the pH paper turns
into red color. With a chemical equations:

Phenol

C6H5OH → CH3CH2O⁻ + H⁺

Ethanol
CH3CH2CH3 → CH3CH2O⁻ + H⁺

Oxidation with Chromic Acid

When Ethanol was added with a Potassium dichromate (K2Cr2O7+ H2SO4) it produces green
precipitate. Also for the Isopropyl alcohol when added with Potassium dichromate it produces a
green precipitate. For a reason that a Cr3+ was produced which is chromium (lll). For tert-butyl it
does not show any visible result. Due to Chromic acid test was only able to identify the primary
alcohols and secondary alcohols but it is not able to recognize a tertiary alcohol. The Ethanol it is
a primary alcohol because there is only one alkyl group attached to the carbon that carries the OH
substituent. Isopropyl alcohol are secondary alcohol is a secondary alcohol, which has two alkyl
groups on the carbon atom with the OH substituent. While the tert-butyl was a tertiary alcohol,
because tert-butyl was attached to three alkyl groups on the carbon with OH substituent. With a
chemical equations:

Ethanol
K2Cr2O7
CH3CH2CH3OH dilute H2SO4 CH3COH + Cr3⁺ (Chromium (lll), green ppt.)
Isopropyl alcohol
K2Cr2O7
CH3CH(OH)2CH3 dilute H2SO4 CH3C(O)2CH3 + Cr3⁺ (Chromium (lll), green ppt.)

Oxidation with Potassium Permanganate

We used ethanol, isopropyl alcohol, and tert-butyl alcohol. When ethanol was added to with
Potassium Permanganate (KMnO4) it produces a brown precipitate. Also with isopropyl alcohol
it also produces a brown precipitate, however when Potassium Permanganate was added in tert-
butyl it does not show a reaction. The brown precipitate that are produce is due to Manganese
dioxide (MnO2). Another substance that is produced in this test is potassium hydroxide (KOH).
Potassium Permanganate turns primary and secondary alcohols into acetic acids. While tertiary
Alcohols does not oxidized which is the tert-butyl. With a chemical equations:

Ethanol

CH3CH2CH3OH + KMnO4 → CH3OOOH + KOH + MnO2 (Brown ppt.)

Isopropyl Alcohol

CH3CH(OH)2CH3 + KMnO4 → CH3OCH3 + KOH + MnO2 (Brown ppt.)

Reaction with Lucas Reagent

Lucas reagent test differentiates reactivity of the three classes of alcohols towards hydrogen
halide. We added the ethanol, isopropyl alcohol, and tert-butyl alcohol a Lucas reagent which
is a mixture of Hydrogen chloride (HCl) and Zinc chloride (ZnCl2). The fastest to react is the
tert-butyl it, reacted to the reagent immediately, followed by Isopropyl alcohol and slowest is
the ethanol. Tertiary alcohols react almost immediately as they form tertiary carbocation
which are the most stable. Cloudiness of the solution is observed in seconds.
Secondary alcohols form white cloudiness of the solution after about 5 minutes as the
secondary carbocation is comparatively less stable.
The primary carbocation being the least stable react very slowly and primary alcohols take a
lot of time to show cloudiness of the solution. With a chemical equations:
TERT-BUTYL
ZnCl2,
C4H10O C4H10Cl
HCl

Properties of Phenol

Ferric chloride Test

Ferric chloride test was a test for phenols and its derivatives. When phenol, resorcinol, salicylic
acid, and ethyl alcohol was added with Ferric chloride (FeCl3). It produces a violet/purple
precipitates but not ethanol. Acidic nature of ethanol. But acidic character of aliphatic alcohol like
ethanol decreases due to +I effect of hydrocarbon. Also formation of alkoxide ion is not favorable.
It is because of development of negative charge in electronegative oxygen atom which makes it
unstable. So, the reaction is unstable. However, phenol can show this reaction. It is because the
formation of phenoxide ion is possible. It has opposite conditions as compared to the aliphatic
acid. With a chemical equations:

H
OH O
FeCl3 FeCl3

phenol
H
OH O
FeCl3 FeCl3

OH OH
resorcinol H
OH O
FeCl3 FeCl3

COOH COOH
salicylic acid

Esterification with Glacial Acetic Acid.

Ethanol was added with Glacial acetic acid (CH3COOH) and concentrated Sulfuric acid (H2SO4)
and placed it with a water bath for few minutes it produces a sweet-smelling/ fruity odor. Ethanol
(CH3CH2CH3OH) is an alcohol and glacial is a carboxylic acid when they are added up they
result in the formation of ester which is a sweet smelling compounds, that is when fruity odor/
sweet smelling is observed. With a chemical equations:
Ethyl Alcohol

𝐂𝐨𝐧𝐜.𝐇𝟐𝐒𝐎𝟒
CH3CH2OH + CH3COOH CH3OOCH2CH3 (Sweet smelling odor/fruity odor) + H20

Conclusion

Therefore, we were able to determined that ethyl alcohol, isopropyl alcohol, and tert-butyl were
more soluble in water which are the positive result for solubility test, compare to n-butyl alcohol,
phenol, and benzyl alcohol. Ethanol that contains 95% was the complete combustion and produced
a blue flame and without a soot, while the 45% ethanol was the incomplete combustion and
produced a yellow flame and a soot. The phenol was more acidic than alcohol because it turns blue
litmus paper to a red color, which is positive result for acidity. In oxidation of alcohols using the
chromic acid, the positive sample are ethanol and isopropyl alcohol because it produced a green
precipitate. In reaction with potassium permanganate ethanol and isopropyl alcohol is the positive
result because it produces a brown precipitate. In formation of alkyl-halide by Lucas reagent the
tert-butyl was the fastest to produce a cloudiness formation in the solution. The Ferric chloride test
positive sample were phenol, resorcinol, and salicylic acid because it produces a violet/purple
precipitate. In esterification of glacial acetic acid test, the ethanol react with carboxylic group it
produces a sweet-smelling / fruity odor.

References:
https://www.google.com/search?q=ferric+chloride+test+for+phenol,+resorcinol,+salicylic+acid+and+eth
yl+alcohol&safe=active&source=lnms&tbm=isch&sa=X&ved=0ahUKEwjI8LeT7PHhAhWBN48KHXjJBMkQ
_AUIDigB&biw=1517&bih=730#imgrc=5PctNtlhYbxwHM:

https://www.google.com/search?q=alcohol+and+phenols&oq=alcohol&aqs=chrome.4.69i59l2j69i57j69i
60j69i59j69i60.9897j0j9&sourceid=chrome&ie=UTF-8

https://www.google.com/search?safe=active&ei=4SDFXN67EYi7rQGsq4TACA&q=properties+of+alcohol
s+and+phenols&oq=alcohol+and+phenols&gs_l=psy-ab.1.0.0i71l8.0.0..92457...0.0..0.0.0.......0......gws-
wiz.yyvLY0wMbnM

BOJO, A. L. (2014). Organic Chemistry Laboaratory manual.Chemistry 23, pp. 27-29. Musuan, Bukidnon:
CMU INSTRUCTIONAL MATERIALS DEVELOPMENT CENTER CENTRAL MINDANAO UNIVERSITY.
 ALCOHOLS AND PHENOLS

Reycel May F. Pañares

Ms. Emma O. Buncales

CHY. 42.1

Tuesday- Thursday-7:00 am- 10:00 am