Department of Chemical Engineering

School of Engineering and Architecture

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one of the hydrogen atoms has been replaced by an alkyl group, typically represented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

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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.

III. Materials

A. Drawing/Illustration of Set-up

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

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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 Equipment)

is a halochromic chemical compound added in small amounts to a

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

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.

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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.

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.

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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.

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.

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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

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.

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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

Alcohol Immediately upon After standing After standing

standing for 5 mins. for 30 mins.

1* Clear Clear Formation of 2

layers

2* Clear Formation of 2

layers

3* Formation of 2

layers

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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

Methyl alcohol No reaction

Ethyl alcohol Yellow precipitate (Positive test with

iodoform)

Acetone Yellow precipitate (Positive test with

iodoform)

Propyl alcohol No reaction

Isopropyl alcohol Yellow precipitate (Positive test with

iodoform)

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E. Acidity of Alcohols and Phenols

F. Reation with Ferric Chloride

VI. Analysis of Results

VII. Conclusion and Recommendation

VIII. Appendices

A. Definition of Terms
B. Documentation
C. Computation

IX. Bibliography/ References

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