Course Code: PHA 034 Lec.

SAS Module # 6

Nam: Class number: _______

Section: ____________ Schedule: Date:
________________________________________ ________________

Lesson title: Alcohols, and Phenols Materials:

Pen and SAS
Lesson Objectives: At the end of the lesson you
should be able to: References:
1. recognize the names of the common  H. Stephen Stoker. Exploring General,
alcohols. Organic, and Biological Chemistry
2. Identify the product form based on the location (2010). Brooks/Cole, Cengage Learning
of hydroxyl group.  George I. Sackheim, Dennis D. Lehman.
3. discuss how to name alcohol and phenols using Chemistry for Health Sciences (8th ed.)
IUPAC And common name. Pearson Education Asia Pte.Ltd.
 Katherine J. Denniston, Joseph J.
Topping, Robert L. Caret. General,
Organic and Biochemistry (5th ed.)
McGraw-Hill Education (Asia)

Productivity Tip:
Schedule doing practice drills similar to the ones in this module two more times this week. Spacing your
practice time will help you master the process.

A. LESSON PREVIEW/REVIEW

Introduction (2 mins)

In this module we study the first two that consider hydrocarbon derivatives with oxygen-
containing functional groups and focuses on hydrocarbon derivatives whose functional groups contain
one oxygen atom participating in two single bonds. In this module also we study the physical and
chemical properties of alcohols, and phenols.

Activity 1: What I Know Chart, part 1 (5 mins)

Instructions: In this chart, reflect on what you know now. Do not worry if you are sure or not sure of your
answers. This activity simply serves to get you started on thinking about our topic. Answer only the first
column, “What I know”. Leave the third column “What I Learned” at this time.

What I Know Questions: What I Learned (Activity 4)

1What is alcohol?

2. What is phenol?

3. What are the uses of alcohol?

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B.MAIN LESSON

Activity 2: Content Notes (40 mins)

Bonding characteristics of the oxygen atom is a prerequisite to our study of compound with
oxygen containing functional groups. Normal bonding behaviour for oxygen atoms in such functional groups is
the formation of two covalent bonds. Oxygen atom can form either two single bonds or double bonds.

Two single bonds one double bond

In organic chemistry, carbon forms four bonds, hydrogen forms one bond, and oxygen forms two bonds.

4 valence electrons 1 valence electron 6 valence electrons

4 covalne bonds 1 covalent bond 2 covalent bonds
no nonbonding no nonbonding 2 non bonding
electron pairs electron pairs electron pairs

Alcohol is an organic compound in which an –OH group is bonded to a saturated carbon atom. A
saturated carbon atom is a carbon atom that is bonded to four other atoms. The general formula of alcohol is
R-OH. The -OH group, is the functional group, is called a hydroxyl group.

Comparison between Hydroxide and Hydroxyl group

HYDROXYL HYDROXIDE

Is a group of atoms that is bonded to a molecule Is an inorganic anion

Always found as a group of atoms bonded to a Can be found in its free forms as an anion
molecule
Can form covalent bonds Can form ionic bonds

Does not have a fixed electrical charge Anion having -1 electrical charge.

Act as functional groups for molecules Ions react with cations in order to form ionic
compounds.

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Example of Structural Formulas for alcohol

CH3-OH CH3-CH2-OH CH3-CH2-CH2-OH
Methyl alcohol Ethyl alcohol propyl alcohol
Methanol Ethanol 1-Propanol

CLASSIFICATION OF ALCOHOLS:

Alcohols are classified as: PRIMARY ALCOHOL (1⁰), SECONDARY (2⁰), and TERTIEARY (3⁰)
alcohol. PRIMARY ALCOHOL is an alcohol in which the hydroxyl –bearing carbon atom is bonded to only
one other carbon atom. SECONDARY ALCOHOL is an alcohol in which the hydroxyl – bearing carbon atom is
bonded to two other carbon atoms. TERTIARY ALCOHOL is an alcohol in which the hydroxyl carbon atom is
bonded to three other carbon atoms.

Example:

PRIMARY ALCOHOL SECONDARY ALCOHOL TERTIARY ALCOHOL

CH3
CH3-OH CH3-CH2-CH2-CH -CH3
CH3-CH2-CH2-C OH
CH3-CH2-CH2-OH OH
CH3
CH3 CH3
CH3-CH2-CH2-CH2CH2-OH CH3
CH3-CH-CH2-CH -CH2-CH-CH3
CH3-CH2-CH2-C-CH3
CH3-CH2-CH2-CH2 OH
OH
OH
OH

NOMENCLATURE FOR ALCOHOLS: Common Name

Rule 1: Name all of the carbon atoms of the molecule as a single alkyl group.

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Rule 2: Add the word alcohol, separating the words with a space.

Note: Common names exist for alcohols with simple (generally C1 to C4) alkyl groups.

Example: OH

CH3-OH – Methyl alcohol CH3-CH2-OH – Ethyl Alcohol -Cyclobutyl alcohol

IUPAC rules for naming alcohols that contain a single hydroxyl group follow.

Rule 1: Name the longest carbon chain to which the hydroxyl group is attached. The chain is obtained by
dropping the final –e from the alkane name and adding the suffix –ol.

Example:
CH3-OH –Methanol CH3-CH2-OH – Ethanol

Rule 2: Number the chain starting at the end nearest the hydroxyl group, and use the appropriate number to
indicate the position of –OH group.

Note: In numbering of the longest carbon chain, the hydroxyl group has priority over double and triple
bonds, as well as over alkyl, cycloalkyl, and halogen substituents.)

Example:

2-Ethyl-1-butanol 2,5-Dimethyl-3-hexanol

5-Methyl-4-octanol

Rule 3: Name and locate any other substituent present.

Rule 4: In alcohols where the –OH group is attached to a carbon atom in a ring, the ring is numbered
beginning with the –OH group.
Numbering then proceeds in a clockwise or counterclockwise direction to give the next substituent
the lower number.
The number “1” (for the hydroxyl group) is omitted from the name since by definition the hydroxyl-
bearing carbon atom is carbon 1.

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Example:

Cyclohexanol 3-Bromocyclohexanol 1,2-Dimethylcyclopentanol

IUPAC and COMMON NAMEs of Monohydroxy Alcohols that contain up to four Carbon Atoms
FORMULA IUPAC NAME COMMON NAME
One carbon atom (CH3-OH)
CH3-OH Methanol Methyl alcohol
Two carbon atoms(C2H5OH)
CH3-CH2-OH Ethanol Ethyl alcohol
Three carbon atoms (C3H7OH): two constitutional isomers exist
CH3CH2-CH2-OH 1-Propanol Propyl alcohol
CH3CH-CH2 2-Propanol Isopropyl alcohol

OH
Four Carbon atoms (C4H9OH): four constitutional isomers exist

CH3-CH2CH2-CH2-OH 1-Butanol Butyl alcohol

CH3-CH-CH2-OH 2-Methyl-1-propanol Isobutyl alcohol

CH3
CH3-CH2-CH-OH 2-Butanol sec-butyl alcohol

CH3
CH3

CH3-CH-OH 2-Methyl-2-propanol tert-butyl alcohol

CH3

Alcohols with More than One Hydroxyl Group

Polyhydroxy alcohols - alcohols that possess more than one hydroxyl group can be named with only
a slight modification of the preceding IUPAC rules.

An alcohol in which two hydroxyl groups are present is named as diol. One containing three hydroxyl

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groups is named as a triol.

In these names for diols, triols and so forth, the final –e of the parent alkane name is retained for
pronunciation reasons.

Example:

1,2-Ethanediol 1,2-Propanediol 1,2,3-Propanetriol

In naming alcohols with unsaturated carbon chains, two endings are needed: One for the double or triple bond
and one for the hydroxyl group. The –ol suffix always comes last in the name; that is, unsaturated alcohols
are named as ALKENOLS OR ALKYNOLS

Example

2- Propen-1-ol 5-Hexen-1-ol
Common name: Allyl alcohol

2-Decyn-1-ol 1-Cyclobuten-ol

1-Ethyl-2,3-dimethyl-2-cyclopenten-1-ol 3-Phenyl-4-nonyn-1-ol

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NAME ( IUPAC and DESCRIPTION and PREPARATION USES

COMMON)
Methyl alcohol With one carbon atoms and one –OH group. Simplest Good fuel (racing cars
(Methanol, Wood alcohol, colorless liquid. are fuelled with methyl
alcohol) It is produced via the reaction of H2 and CO. alcohol)
Excellent solvent
properties
Drinking methyl alcohol is very dangerous. Methyl alcohol
Solvent of choice for
will oxidized in the body with the help of the liver enzyme
paints, shellacs, and
called Alcohol dehydrogenase to the toxic metabolites
varnishes.
formaldehyde and formic acid.

Formaldehyde can cause blindness

(temporary or permanent) formic acid causes acidosis.
Ingesting as 30 ml of methyl alcohol can cause nerve
damage.
Ethyl alcohol Two –carbon monohydroxy alcohol. Is the alcohol present in Ethyl alcohol used in
(Ethanol,Grain alcoholic beverages and is commonly reffered to simply as industry rom ethene via
alcohol ) alcohol or drinking alcohol. Ethyl alcohol is oxidized in the hydration reaction.
body by the liver enzyme called alcohol dehydrogenase. Widely used as an
antiseptic.
Used as solvent

Acetaldehyde, the first oxidation product of ethyl alcohol,

responsible for the symptoms of hangover. Ethyl alcohol
oxidation products are less toxic than those of methyl
alcohol.
Ethyl acohol can be produced by yeast fermentation of
sugars found in plant extracts.

Fermentation is the process by which ethyl alcohol for

alcoholic beverages is produced.

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Denatured alcohol is ethyl alcohol that has been rendered

unfit to drink by addition of small amounts of toxic
substances.(denaturing agents).
NOTE: The alcohol content of strong alcoholic beverages is
often stated in terms of proof. PROOF is twice the
percentage of alcohol.
Isopropyl alcohol Is one of two three-carbon monohydroxy alcohols; it is It is used in cosmetics
(2-Propanol) marketed as rubbing alcohol ( 70 % isopropyl alcohol-30 % formulations such as
water solution). It has abitter taste, its toxicity is twice that of after-shave lotion and
ethyl alcohol. In the body it is oxidized to acetone. Large hand lotions.
amounts(150ml) of ingested isopropyl alcohol can be fatal; Since it is not absorbed
death occurs from paralysis of the central nervous system. through the skin, it is
commonly used as a
rubbing alcohol and as
astringent.
Ethylene glycol Are the two simplest alcohols possessing two-OH groups. Use as the main in.
(1,2-ethenediol) Besides being diols, they are classified as glycols. Glycol is gredient in automobile
Propylene glycol a diol in which the two-OH groups are on adjacent carbon year-round”antifreeze
(1,2-Propanediol) atoms. Both of these glycols are colorless, odourless, high- for the manufacture of
boiling liquids that are completely miscible with water. polyester fibers.
Ethylene glycol and Propylene glycol are synthesized from Permanent antifreeze
ethylene and propylene, respectively, hence their common for car radiators
name.
Ethylene glycol is extremely toxic when ingested. In the
body, liver enzymes oxidize it to oxalic acid.

Oxalic acid, as a calcium salt, crystallizes in the kidneys,

which leads to renal problems.
Propylene glycol is essentially nontoxic.
Glycerol It is often called glycerine, is a clear, thick liquid that has It is used in
(1,2,3-Propanetriol consistency of honey. Its molecular structure involves three - pharmaceutical
OH groups on three different carbon atoms. Glycerol is preparations such as
normally present in the human body because it ia a by skin lotions and soaps.

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 Course Code: PHA 034 Lec.
SAS Module # 6

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Section: ____________ Schedule: Date:
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product of fat metabolism. Use in shaving creams,

glycerol suppositories
for rectal administration
of medicines
Used in candies and
icings as a retardant for
preventing sugar
cyrstallizations.

CHEMICAL REACTIONS OF ALCOHOLS

Combustion reaction hydrocarbons of all types
undergo combustion in air to produce carbon dioxide
and water.
INTRAMOLECULA ALCOHOL DEHYDRATION
Dehydration reaction is a chemical reaction in which
the components of water ( H and OH) are removed
from a single reactant or from two reactant (H from
one and OH from the other). In intramolecular
dehydration, both water components are removed
from the same molecule.
Reaction condition: temperature of 180⁰C and the
presence of sulphuric acid (H2SO4) as a catalyst. The
dehydration product is alkene.
Ethyl alcohol are the most difficult to dehydrate,
requiring temperatures around 180⁰C.
Secondary alcohol dehydration occurs at lower
temperatures
Tertiary alcohols dehydrate at temperatures slightly
above the room temperature.
Intramolecular alcohol dehydration is an example of
Elimination reaction.
Elimination Reaction is a reaction in which two groups
or two atoms on neighboring carbon atoms are removed
or eliminated from a molecule, leaving a multiple bond
between the carbon atoms.
Alkene formation via intramolecular alcohol dehydration
is the reverse reaction to the reaction for preparing an
alcohol through hydration of an alkne. Dehydration of an alcohol can result in the
production of more than one alkene product.
Dehydration of 2-Butanol produces two alkenes.

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INTERMOLECULAR ALCOHOL DEHYDRATION

Intermolecular dehydration process can occur to
produce an ether- a compound with general structure
R-O-R, at a lower temperature, 140⁰C than that required
for alkene formation 180⁰C. Example:
Condensation reaction is a chemical reaction in which
two molecules combine to form a larger one while
liberating a small molecule usually water. In this case,
two alcohol molecules combine to form an ether and
water.

The following is a summary of products obtained from alcohol dehydration reactions using sulphuric
acid(H2SO4) as a catalyst.

Oxidation reaction some alcohols readily undergo One hydrogen comes from the –OH group, the other
oxidation with mild oxidizing agents; others are resistant from the carbon atom to which the –Oh group is
with these mild oxidizing agents. attached. This H removal generates a carbon
Primary and Secondary alcohols, but not Tertiary oxygen double bond.
alcohol readily undergo oxidation in the presence of
mild oxidizing agents to produce compounds that

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contain a carbon-oxygen double bond ( aldehydes,

ketones and carboxylic acids).
Oxidizing agents that can be used for the oxidation
reaction, including: Potassium permanganate
(KMnO4), Potassium dichromate (K2Cr2O7)), and
Chromic acid (H2CrO4).
An organic oxidation is an oxidation that increases the
number of C-O bonds and/or decreases the number of
C-H bonds.
An organic reduction is a reduction that increases the
number of C-O bonds and/or increases the number of
C-H bonds.
TWO TYPES OF OXIDIZABLE ALCOHOLS, YIELD
DIFFERENT PRODUCTS.

Primary alcohol (1⁰) produces an aldehyde that is

often further oxidized to carboxylic acid.

General Reaction for the oxidation of a primary

alcohol.

Secondary alcohol (2⁰) produces ketones.

Tertiary alcohol no reaction to mild oxidizing agent.

Halogenation alcohols undergo halogenations reaction

in which a halogen atom is substituted for the hydroxyl
group, producing an alkyl halide.

PHENOLS

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Is an organic compound in which an –OH group is attached to a carbon atom that is part of an
aromatic carbon ring system. The general formula for phenols is Ar-OH, where Ar represents an aryl group.
Aryl group is an aromatic carbon ring system from which one hydrogen atom has been removed.
Hydroxy group is thus the functional group for both phenols and alcohols.

Example of compounds classified as phenols:

NOMENCLATURE FOR PHENOLS

RULES:
• Parent name is Phenol.
• Ring numbering begins with the –OH group and proceeds in the direction that gives the lower number
to the next carbon atom bearing a substituent.
• The numerical position of the –OH group is not specified in the name because it is 1 by definition.

SPECIAL NAMES

HYDROXYPHENOLS

PHYSICAL AND CHEMICAL PROPERTIES OF PHENOLS:

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Phenols are generally low-melting solids or oily liquids at room temperature. Most of them are slightly
soluble with water. Many phenols have antiseptic and disinfectant properties. Phenol is a colorless solid with a
medicinal odor. Both alcohols abd phenols are flammable, phenols cannot be dehydrated, do not react with
oxidizing agents, phenols can be oxidized by stronger oxidizing agents. Acidity is one of the most important
properties of phenols. Phenols are weak acids in solution.
The acid ionization reaction for phenol itself is:

NOTE: the negative ion produced from the ionization is called the Phenoxide ion. Sodium phenoxide is
produced when phenol react with sodium hydroxide ( a base).

OCCURRENCE AND USES FOR PHENOLS

Dilute 2% solutions of phenols used as antiseptics. Concentrated phenol solutions however can cause
severe skin burns.
The compound 4-Hexylresorcinol is an ingredient in many mouthwashes and throat lozenges.

Phenol derivatives o-phenylphenol and 2-benzyl-4-chlorophenol are the active ingredients in Lysol, a
disinfectant for walls, floors and furniture in homes and hospitals.

A number of phenols possess antioxidant activity

Two Commercial phenolic antioxidant food additives:

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BHA ( butylated hydroxyl anisole)

BHT (butylated hydroxyl toluene

Vitamin E is a naturally occurring antioxidant that is

important in
the functioning of the human body.

Phenols found in plants are used as flavoring agents and/or antibacterials.

Thymol obtained from the herb thyme, possesses both

flavorant and Antibacterial
properties.
It is used as an ingredient in several mouthwash
formulations.

Isoeugenol, which differs only in structure from eugenol

only in the location of the
double bond in the hydrocarbon side chain.
Responsible for the odor assocaited with nutmeg.

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Eugenol is responsible for the flavor of cloves. Dentists

traditionally used Clove
oil as an antiseptic.

vanillin gives vanilla its flavor, extracted from the dried

seed pods of the vanilla
orchid.
Synthetic vanillin is produced by oxidation of eugenol .

Activity 3: Skill-building Activities (with answer key) (30 mins + 5 mins checking)

I. A- Classify each of the following alcohols as: Primary, Secondary and Tertiary alcohol. Check your
answers against the Keys to Correction found in the last pages of this SAS. Write your Score.
1. 1-Pentanol

2. 2-Methyl-1-pentanol

3. 2-Pentanol

4. 2-Methyl-1-butanol

5. 1-butanol

II. B- Assign IUPAC name to each of the following polyhydroxy alcohols: Check your answers against
the Keys to Correction found in the last pages of this SAS. Write your Score

1. CH2-CH-CH3

OH OH

2. CH2-CH2-CH2-CH-CH3

OH OH

3. CH3-CH2-CH-CH2-CH2

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OH OH

4. CH2-CH-CH-CH2

OH OH CH3OH

OH

5.

Activity 4: What I Know Chart, part 2 (3 mins)

Instruction: To review what was learned from this session, please go back to Activity 1 and answer the “What I
Learned “column. Notice to reflect on any changes in your answers.

Activity 5: Check for Understanding (30 mins.)

A- Each of the following alcohols is named incorrectly. Give the correct IUPC name for each alcohol.

1. 1-Ethyl-1-butanol

2. 1-Methyl-2,4-butanediol

3. 1-Methyl-3-butanol

4. 1,4-Cyclopentanediol

5. 3-Propyl-2-butanol

B-Classify each of the following alcohols as: primary, secondary and tertiary alcohol.
OH OH OH

1. 3. 5.
CH3
OH

2. 4.

Br HO CH3

C- Identify if the Oxidation product form is: Aldehydes, Ketones and no reaction.

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1. 1-Pentanol

2. 3-Methyl-2-hexanol

3. 2-Octanol

4. 2-Methyl-2-propanol

5. Pentanol

C. LESSON WRAP-UP

Activity 6: Thinking about Learning (5 mins)

A. Work Tracker: You are done with this session! Let’s track your progress. Shade the session
number you just completed.
Reminder: Instructor/Facilitator. Please direct the student to mark their place in the work tracker
which is simply a visual to help students track how much work they have accomplished and how
much work there is left to do.

P1 P2
1 2 3 4 5 6 7 8 9 10

B. Think about your Learning: Tell me what part of the module that you think I need to discussed or
elaborate further, and why?

FAQs

1. What are some common alcoholic beverages available in the market and indicate the ethyl alcohol
content (volume percent)?
Ans. The 3 common alcoholic beverages are: Beer – 3.2-9, Wine -12, Rum -45.

2. What are the classifications of alcohol as to the no. of hydroxyl group present?
Ans. The classifications of alcohol according to the no. of hydroxyl group present are: Monohydroxy
alcohol, Dihydroxy alcohol and Polyhydroxy alcohol

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KEY TO CORRECTIONS for Activity no. 3:

A- Classify each of the following alcohols as: Primary, Secondary and Tertiary alcohol.

1. 1-Pentanol

2. 2-Methyl-1-pentanol

3. 2-Pentanol

4. 2-Methyl-2-butanol

5. 1-butanol

Answers: 1. Primary alcohol 2. Primary alcohol 3. Secondary alcohol 4. Tertiary alcohol, 5. Primary alcohol

B- Assign IUPAC name to each of the following polyhydroxy alcohols:

1. CH2-CH-CH3 Ans. 1,2-Propanediol

OH OH

2. CH2-CH2-CH2-CH-CH3 Ans.1,4-Pentanediol

OH OH

3. CH3-CH2-CH-CH2-CH2 Ans. 1,3- pentanediol

OH OH

4. CH2-CH-CH-CH2 Ans. 3-Methyl-1,2,4-butanetriol

OH OH CH3OH

OH OH

5. Ans. 3-Methyl-2,6-heptanediol

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