Department of Chemical Engineering

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Saint Louis University

LABORATORY REPORT EVALUATION SHEET

Laboratory Course: Organic Chemistry (CHEM 2121L) Schedule: 01:30 - 04:30 MW

Experimental Number: 10
Experiment Title: Alcohols and Phenols
Group Number: 5
Group Members: Mutia, Jerico Date Performed:
Pelayo, Jonh Vincent Date Submitted: ______________
Resurreccion, Bill Llonard
Rosendo, Rocel
Niduaza, Marife
Pardilla, Shaina
Regacho, Anjanette

TOTAL
CONTENTS REMARKS SCORE
POINTS

I. OBJECTIVE 5

II. THEORETICAL
15
BACKGROUND
III. MATERIALS:
A. DRAWING/
ILLUSTRATION OF
10
SET-UP
B. CLASSIFICATION
AND USES
IV. METHODOLOGY/
10
PROCEDURE

V. DATA AND RESULTS 15

VI. ANALYSIS OF
RESULTS
15

VII. CONCLUSION AND

10
RECOMMENDATION

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VIII. APPENDICES:
A. DEFINITION OF
TERMS 10
B. DOCUMENTATION
C. COMPUTATION
IX. BIBLIOGRAPHY/
5
REFERENCES
X. FORMAT AND
5
NEATNESS

TOTAL POINTS: 100 SCORE:

Evaluated by: Engr. Vera Lee Mendoza Date: Sept. 25, 2019

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I. Problem Statement/Objective

The main objective of the experiment is to observe and determine the classifications

of Alcohols. The experiment also intends to examine the physical and chemical

properties of the representative alcohols and phenols and to compare the chemical

behavior between these compounds.

II. Discussion/Theoretical Background

Alcohols

Alcohol, any of a class of organic compounds characterized by one or more

hydroxyl (―OH) groups attached to a carbon atom of an alkyl group (hydrocarbon

chain). Alcohols may be considered as organic derivatives of water (H2O) in which

one of the hydrogen atoms has been replaced by an alkyl group, typically represented

by R in organic structures. For example, in ethanol (or ethyl alcohol) the alkyl group is

the ethyl group, ―CH2CH3.

Alcohols are among the most common organic compounds. They are used as

sweeteners and in making perfumes, are valuable intermediates in the synthesis of other

compounds, and are among the most abundantly produced organic chemicals in

industry. Perhaps the two best-known alcohols are ethanol and methanol (or methyl

alcohol). Ethanol is used in toiletries, pharmaceuticals, and fuels, and it is used to

sterilize hospital instruments. It is, moreover, the alcohol in alcoholic beverages. The

anesthetic ether is also made from ethanol. Methanol is used as a solvent, as a raw

material for the manufacture of formaldehyde and special resins, in special fuels, in

antifreeze, and for cleaning metals.

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Alcohols may be classified as primary, secondary, or tertiary, according to which

carbon of the alkyl group is bonded to the hydroxyl group. Most alcohols are colourless

liquids or solids at room temperature. Alcohols of low molecular weight are highly

soluble in water; with increasing molecular weight, they become less soluble in water,

and their boiling points, vapour pressures, densities, and viscosities increase. Most of

the common alcohols are colourless liquids at room temperature. Methyl alcohol, ethyl

alcohol, and isopropyl alcohol are free-flowing liquids with fruity odours. The higher

alcohols—those containing 4 to 10 carbon atoms—are somewhat viscous, or oily, and

they have heavier fruity odours. Some of the highly branched alcohols and many

alcohols containing more than 12 carbon atoms are solids at room temperature. Because

alcohols are easily synthesized and easily transformed into other compounds, they

serve as important intermediates in organic synthesis. A multistep synthesis may use

Grignard-like reactions to form an alcohol with the desired carbon structure, followed

by reactions to convert the hydroxyl group of the alcohol to the desired functionality.

The most common reactions of alcohols can be classified as oxidation, dehydration,

substitution, esterification, and reactions of alkoxides.

Phenols

Phenol, any of a family of organic compounds characterized by a hydroxyl (―OH)

group attached to a carbon atom that is part of an aromatic ring. Besides serving as the

generic name for the entire family, the term phenol is also the specific name for its

simplest member, monohydroxy benzene (C6H5OH), also known as benzenol, or

carbolic acid. Phenols are similar to alcohols but form stronger hydrogen bonds. Thus,

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they are more soluble in water than are alcohols and have higher boiling points. Phenols

occur either as colourless liquids or white solids at room temperature and may be highly

toxic and caustic. Phenols are widely used in household products and as intermediates

for industrial synthesis. For example, phenol itself is used (in low concentrations) as a

disinfectant in household cleaners and in mouthwash. Phenol may have been the first

surgical antiseptic. In 1865 the British surgeon Joseph Lister used phenol as an

antiseptic to sterilize his operating field. With phenol used in this manner, the mortality

rate from surgical amputations fell from 45 to 15 percent in Lister’s ward. Phenol is

quite toxic, however, and concentrated solutions cause severe but painless burns of the

skin and mucous membranes. Less-toxic phenols, such as n-hexylresorcinol, have

supplanted phenol itself in cough drops and other antiseptic applications. Butylated

hydroxytoluene (BHT) has a much lower toxicity and is a common antioxidant in

foods.

Phenols are common in nature; examples include tyrosine, one of the standard

amino acids found in most proteins; epinephrine (adrenaline), a stimulant hormone

produced by the adrenal medulla; serotonin, a neurotransmitter in the brain; and

urushiol, an irritant secreted by poison ivy to prevent animals from eating its leaves.

Many of the more complex phenols used as flavourings and aromas are obtained from

essential oils of plants. For example, vanillin, the principal flavouring in vanilla, is

isolated from vanilla beans, and methyl salicylate, which has a characteristic minty

taste and odour, is isolated from wintergreen. Other phenols obtained from plants

include thymol, isolated from thyme, and eugenol, isolated from cloves. Similar to

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alcohols, phenols have hydroxyl groups that can participate in intermolecular hydrogen

bonding; in fact, phenols tend to form stronger hydrogen bonds than alcohols. (See

chemical bonding: Intermolecular forces for more information about hydrogen

bonding.) Hydrogen bonding results in higher melting points and much higher boiling

points for phenols than for hydrocarbons with similar molecular weights. For example,

phenol (molecular weight [MW] 94, boiling point [bp] 182 °C [359.6 °F]) has a boiling

point more than 70 degrees higher than that of toluene (C6H5CH3; MW 92, bp 111 °C

[231.8 °F]). The ability of phenols to form strong hydrogen bonds also enhances their

solubility in water. Phenol dissolves to give a 9.3 percent solution in water, compared

with a 3.6 percent solution for cyclohexanol in water. The association between water

and phenol is unusually strong; when crystalline phenol is left out in a humid

environment, it picks up enough water from the air to form liquid droplets.

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III. Materials

A. Drawing/Illustration of Set-up

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B. Classification and Uses

The equipments used in this experiment are the same with the equipments used in

the previous experiment:

 Beaker (Glassware)

A beaker is generally a cylindrical container with a flat bottom. Most

also have a small spout to aid pouring, as shown in the picture. Beakers are

available in a wide range of sizes, from one milliliter up to several liters. A

beaker is distinguished from a flask by having straight rather than sloping

sides.

 Bunsen Burner (Heating Equipment)

A Bunsen burner, named after Robert Bunsen, is a common piece of

laboratory equipment that produces a single open gas flame, which is used

for heating, sterilization, and combustion.

 Dropper (Measuring Equipment)

is a pipette consisting of a small tube with a vacuum bulb at one end

for drawing liquid in and releasing it a drop at a time.

 pH Paper (Testing Material)

is a halochromic chemical compound added in small amounts to a

solution so the pH (acidity or basicity) of the solution can be determined

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visually. Hence, a pH indicator is a chemical detector for hydronium ions

(H3O+) or hydrogen ions (H+) in the Arrhenius model.

 Test Tube (Glassware Container)

The head of safety matches are made of an oxidizing agent such as

potassium chlorate, mixed with sulfur, fillers and glass powder. The side of

the box contains red phosphorus, binder and powdered glass.

IV. Methodology/Procedure

A. Solubility

1. Put 5-drop samples of the following into separate, labeled test

tubes: Ethyl alcohol, isopropyl alcohol, t-butyl alcohol, ethylene

glycol, benzyl alcohol and resorcinol.

2. To each tube, add 1-2 ml of distilled water, mix thoroughly. Record

your observations.

3. Repeat procedure 1 and add to each test tubes 5 drops of ether.

Record your observations.

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B. Lucas Test (ZnCl2 in concentrated HCl)

1. Put 5-drop samples of the following into separate, labeled test

tubes: Ethyl alcohol, isopropyl, t-butyl alcohol, resorcinol.

2. Add 10 drops of Lucas reagent to each sample and mix the contents

well by agitation. Note the time until a chemical change takes place.

Lucas Reagent contains concentrated HCl that will vigorously

damage tissue. Contact should be avoided. If you get any on your

skin, wash it off immediately with cool water and inform your

instructor.

3. Put any tubes with clear solutions into a boiling water bath and

observe again after heating for two minutes.

4. Record your observation.

C. Oxidation (Bordwell-Welman Test)

1. Put 5-drop samples of the following into separate, labeled test

tubes: Ethyl alcohol, isopropyl alcohol, t-butyl alcohol, resorcinol.

2. Add 10 drops of reagent grade acetone to each test tube.

3. Shake each test tube to mix the contents.

4. Add 5 drops of potassium dichromate.

5. Acidify with 2 drops of concentrated sulfuric acid. (Caution: Use

Gloves with concentrated sulfuric acid.)

6. Observe the test tubes after 3 minutes and record your observation.

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D. Iodoform Test

1. Put 10 drops of the following compounds into separate test tubes:

Ethyl alcohol, propyl alcohol, isopropyl alcohol, phenol.

2. Add 20 drops of I2 – KI solution to each tube and mix thoroughly.

3. To each test tubes, add 5 drops of 10% NaOH solution. Mix well.

Observe for any color changes or precipitation.

4. Record your observation in table 12- 4.

E. Acidity of Phenols

1. Place 5-drop samples each of ethyl alcohol, liquid phenol and

resorcinol into separate test tubes.

2. Add 20 drops of distilled water to each test tube and mix thoroughly.

3. Place 20 drops of distilled water to a separate clean test tube.

4. Using wide – range pH paper, measure the pH of each solution and

that of the pure water.

5. Record each pH value.

F. Reaction with Ferric Chloride

1. Place 5-drop samples each of isopropyl alcohol, liquid phenol and

resorcinol, diluted salicylic acid solution

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2. Add 20 drops of distilled water to each test tube and mix thoroughly.

3. To each, add 2 drops of ferric chloride solution, swirl the contents

and record the results.

V. Data and Results

A. Solubility

Alcohol Water Ether

Ethyl alcohol Miscible Miscible

Benzyl alcohol Moderately Miscible Miscible

Isopropyl alcohol Miscible Miscible

t-butyl alcohol Miscible Miscible

Ethylene glycol Miscible Miscible

B. Lucas Test

Sample Appearance within the Appearance after 2 –

first minute. minutes heating

onwards.

Ethyl alcohol No layer, clear solution No reaction

Isopropyl No layer, clear solution Cloudy solution, layered

t-butyl alcohol Cloudy solution, layered

Resorcinol No layer, clear solution No reaction

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C. Oxidation

Sample Result of adding acidified potassium

dichromate

Ethyl alcohol Dark green coloration

Benzyl alcohol Dark green coloration

Isopropyl alcohol Dark green coloration

t-butyl alcohol No reaction

D. Iodoform Test

Sample Result of adding I2-KI solution

Ethyl alcohol Yellow precipitate – positive result

Propyl alcohol Clear solution – negative result

Isopropyl Yellow precipitate – positive result

Phenol Clear solution – negative result

E. Acidity of Alcohols and Phenols

Sample pH of sample Acid, Base or Neutral

Ethyl Alcohol 5 Weak acid

Phenol 6 Weak acid

Resorcinol 1 Strong acid

Water 7 Neutral

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F. Reation with Ferric Chloride

Sample Result of adding Ferric Chloride

Isopropyl alcohol Yellow coloration – negative result

Phenol Violet coloration – positive result

Resorcinol Yellow coloration – negative result

Salicylic acid Violet coloration – positive result

VI. Analysis of Results

Solubility is a chemical property referring to the ability for a given substance, the

solute, to dissolve in a solvent. In the test for solubility of the five alcohol samples

which are Ethyl alcohol, benzyl alcohol, isopropyl alcohol, t-butyl alcohol and ethylene

glycol, all are miscible in water and ether.

Lucas test is a test used in determining the primary, secondary and tertiary alcohol.

In the Lucas test, primary alcohols will form 2 layers after standing for 30 minutes;

secondary alcohol will form 2 layers after standing for 5 minutes and tertiary alcohols

will immediately form 2 layers.

Primary Alcohol: Ethyl alcohol; Benzyl alcohol

Secondary Alcohol: Isopropyl alcohol

Tertiary Alcohol: t-butyl alcohol

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Adding acidified potassium dichromate to ethyl alcohol (primary alcohol) and

isopropyl alcohol (secondary alcohol) resulted in a Dark green coloration of the

solution while in adding acidified potassium dichromate to t-butyl alcohol (tertiary

alcohol) and resorcinol (phenol) resulted in no reaction.

Iodoform test is a test for the presence of carbonyl compounds with the structure

RCOCH3 and alcohols with the structure RCH(OH)CH3. In the Iodoform Test, the

students added I2-KI solution or Potassium triiodide to Ethyl alcohol, isopropyl

alcohol, t-butyl alcohol and resorcinol. The results are the following:

Ethyl alcohol: Positive test with iodoform.

Isopropyl alcohol: Positive test with iodoform.

t-butyl alcohol: No reaction.

Resorcinol: Positive test with iodoform.

In the acidity of alcohols and phenols, the test found out that resorcinol is the most

acidic compared to other samples. The other samples were ethyl alcohol and phenol

which are weak acids based on the test that was performed.

In adding Ferric chloride in Isopropyl alcohol and resorcinol, it gave a result of

yellow coloration of the solution and considered as negative result while in adding

ferric chloride to phenol and salicylic acid, it gave a result of violet coloration of the

solution, a positive result.

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VII. Conclusion and Recommendation

The first test conducted is the solubility test where water and ether are the solvent.

Test compounds used were ethyl alcohol, benzyl alcohol, isopropyl alcohol, t-butyl

alcohol and ethylene glycol. It was found that all of these samples are miscible in the

solvents that were used. This is due to the hydroxyl group in the alcohol which is able

to form hydrogen bonds with water molecules.

In the acidity/basicity test, it was found that phenol is more acidic than ethanol.

These can also be seen when pH paper was tested on both compounds. The reason for

this was the concept of resonance. When phenol was deprotonated, it still has stable

conjugate base making it more acidic compared to ethyl alcohol. Moreover, phenol

produced more resonance structures than that of ethyl alcohol.

In oxidation test, the test compounds were oxidized using 1% aqueous potassium

chromate added in dilute sulfuric acid. T-butyl alcohol did not show any presence of

reaction since it cannot be further oxidized. Ethyl alcohol was oxidized into ethanal

and isopropanol oxidized into acetone. It can be said that only primary and secondary

alcohols are reactive in this test.

The last test performed was the ferric chloride test. Phenol was reactive producing

violet solution while benzyl alcohol was unreactive. This is an excellent test for

differentiating alcohols from phenols.

The objectives of this experiment were met which were to examine and differentiate

the properties of alcohols and phenols and to visualize the characteristic reactions of

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alcohols and phenols. It can be recommended that the reactions must be observed for a

longer period of time since the other reactions were not totally completed.

It can be recommended that reactions can be performed only if the reagents used

are free from any contaminations. These can be done by performing the experiment

under the fume hood and avoiding exposure to air. Any reactions using contaminated

reagents will induce erroneous results.

VIII. Appendices

A. Definition of Terms

Acidity - the level of acid in substances.

Alcohol - a colorless volatile flammable liquid that is produced by the natural

fermentation of sugars and is the intoxicating constituent of wine, beer, spirits, and

other drinks, and is also used as an industrial solvent and as fuel.

Iodoform Test - is used to check the presence of carbonyl compounds with the

structure R-CO-CH3 or alcohols with the structure R-CH(OH)-CH3 in a given

unknown substance.

Lucas Test - is a test to differentiate between primary, secondary, and tertiary

alcohols. It is based on the difference in reactivity of the three classes of alcohols

with hydrogen halides via an SN1 reaction: ROH + HCl → RCl + H2O.

Oxidation - the process or result of oxidizing or being oxidized.

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Phenol - a mildly acidic toxic white crystalline solid obtained from coal tar and

used in chemical manufacture, and in dilute form (under the name carbolic) as a

disinfectant.

Solubility - is a chemical property referring to the ability for a given substance, the

solute, to dissolve in a solvent. It is measured in terms of the maximum amount of

solute dissolved in a solvent at equilibrium. The resulting solution is called a

saturated solution.

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B. Documentation

Figure 1. Solubility Test.

Figure 2. Lucas Test.

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Figure 3. Adding Potassium dichromate to isopropyl alcohol (secondary alcohol)

and ethyl alcohol (primary alcohol) results in dark green coloration.

Figure 4. A Positive (violet) and Negative (yellow) result of the addition of Ferric

chloride.

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Figure 5. Testing the Acidity of alcohols and phenols basing it on the pH paper.

Resorcinol is the most acidic compared to other samples.

Figure 6. A tertiary alcohol. No reaction in the addition of potassium dichromate.

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C. Answers to Questions:

1. What general conclusions can you draw about the solubility of alcohols

based on your observation data?

The solubility of alcohol is based on the hydroxyl group that is present in it

that is able to form hydrogen bonding with other molecules. Alcohols with a smaller

hydrocarbon chain are very soluble. As the length of the hydrocarbon chain

increases, the solubility in water decreases. Also, as water is polar it attracts OH

group. Carbon chain on the other hand as nonpolar is repelled. Solubility of

alcohols is therefore determined by the stronger of the two forces.

2. Write the balanced equations for all the organic substances in procedures B

and C.

Procedure B.

Procedure C.

3. What is the purpose of adding acetone in the oxidation of alcohols?

Organic solvents other than acetic acid can be used with aqueous chromium

trioxide. Acetone has been used as a cosolvent in a dilute sulfuric acid solution,

and oxidation of alkynyl carbinols was improved when compared to other

procedures known at that time. Secondary alcohols are oxidized to ketones, and

primary alcohols can be oxidized to either an aldehyde or a carboxylic acid. This

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chromium trioxide/acetone/sulfuric acid reagent is often referred to as the Jones

reagent, and oxidation of alcohols with this reagent is called Jones oxidation. Jones

oxidation is especially useful for molecules that contain alkenyl or alkynyl groups.

Oxidation of alcohols is usually faster in acetone than in acetic acid, and using a

large excess of acetone protects the ketone product from further oxidation. An

example is the oxidation of testosterone to give ketone 11 in 73% yield, taken from

a synthesis of formestane by Martin et al. The secondary alcohol was oxidized to

the ketone and the primary alcohol was simultaneously oxidized to the carboxylic

acid.

4. What simple test can be used to distinguish alcohols from phenols?

Ferric chloride test. We can easily distinguish alcohols and phenols.

Phenols react with ferric chloride in giving violet coloration of the solution.

Alcohols do not produce such deep coloration when treated with ferric chloride

solution.

5. Indicate the results (observations) you would expect from treating each of

the following compounds with Lucas reagent and with chromic acid. Tabulate

your answers.

Sample Addition of Lucas Addition of Chromic

Reagent acid
Ethyl alcohol No reaction Dark green coloration

Isopropyl alcohol Formation of 2 layers Dark green coloration

after 5 minutes

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Tert-butyl alcohol Immediate formation of No reaction

2 layers
Resorcinol No reaction No reaction

Phenol No reaction No reaction

Benzyl alcohol Immediate formation of No reaction

2 layers
Salicylic acid No reaction No reaction

6. Complete the following table:

IUPAC Name Chemical Structure Common Use

Ethyl Ethanol Alcoholic

alcohol Beverages

Isopropyl Propan-2-ol Disinfectant

alcohol

Ethylene 1,2-ethanediol Commercial

alcohol and Industrial
applications.

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Benzyl Phenyl methanol Bacteriostatic

alcohol preservative

Phenol Hydroxybenzene Disinfectant

Resorcinol 1,3-benzenediol Disinfectant

Salicylic NA Preparation of
acid drugs.

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IX. Bibliography/ References

Leroy G. Wade. Phenol; Encyclopedia Britannica.2019

Leroy G. Wade. Alcohol; Encyclopedia Britannica.2019

Wikipedia.org

Chem.Libretext. Org

ScienceDirect.com

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