EXPERIMENT #13

ALCOHOLS
DR. MINA
Introduction of
Alochols
Reminders!
• 1. Assign your leader for Expt. #13 ALCOHOLS
• 2. Study the following presentations for alcohols and answer the task or
guide questions.
• 3. Leaders will collect the individual task and will be submitted together
with the group task via canvas or ceu gmail (hard copy will be collected
as soon as classes resume)
• 4. Always write your Group Number, Name of Leader and Section
• 5. send message in our GC if you have some clarifications or questions.
• 6. Leader in case you & your members have a good internet
connections submit your answer on April 28, 2020.
Organic Compounds that Contain Oxygen,
Halogen, or Sulfur
Four families of compounds that contain a C atom
singly bonded to O, S, or X (F, Cl, Br, or I) are:
1. Alcohols, which contain an OH (hydroxyl) group

CH3-OH METHANOL

4
Structure and Properties of
Alcohols
•Alcohols contain a hydroxyl (OH) group.

•Alcohols are classified by the number of C atoms

bonded to the C with the OH group.

A primary (1o) alcohol has

an OH group on a C bonded
only to 1 C atom.
1o
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Structure and Properties of
Alcohols

A secondary (2o) alcohol has

an OH group on a C bonded
only to 2 C atoms.

2o

A tertiary (3o) alcohol has

an OH group on a C bonded
3o only to 3 C atoms.

6
Structure and Properties of
Alcohols
•An alcohol contains an O atom with a bent shape
like H2O, with a bond angle of 109.5o.

•Alcohols have two polar bonds, C—O and O—H,

with a bent shape, therefore it has a net dipole.

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Structure and Properties of
Alcohols
•Alcohols have an H atom bonded to an O atom,
making them capable of intermolecular hydrogen
bonding.

•All of these properties give alcohols much stronger

intermolecular forces than alkanes and alkenes.

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Structure and Properties of
Alcohols
•Alcohols are soluble in organic solvents.
•Low molecular weight alcohols (6 C’s or less)
are soluble in water.
•Higher molecular weight alcohols (6 C’s or more)
are not soluble in water.

2 C’s in chain 8 C’s in chain

water soluble water insoluble
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Structure and Properties of
Alcohols
•Therefore, alcohols have higher boiling and melting
points than hydrocarbons of comparable size and
shape.

stronger intermolecular forces

higher boiling and melting point
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Nomenclature of Alcohols
HOW TO Name an Alcohol Using the IUPAC System

Example Give the IUPAC name of the following alcohol.

Find the longest carbon chain containing the

Step [1]
C bonded to the OH group.

•Change the –e ending of

the parent alkane to the
6 C’s in longest chain suffix –ol.
hexane ----> hexanol 11
Nomenclature of Alcohols
HOW TO Name an Alcohol Using the IUPAC System
Number the carbon chain to give the OH group
Step [2]
the lower number, and apply all other rules
of nomenclature.

Answer
3-hexanol
5-methyl-3-hexanol

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Nomenclature of Alcohols

•When an OH group is bonded to a ring, the OH

is automatically on C1.

•The “1” is usually omitted from the name.

•The ring is then numbered to give the next

substituent the lower number.

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Nomenclature of Alcohols

•Common names are often used for simple alcohols.

•Name all the C atoms of the molecule as a single

alkyl group.

•Add the word alcohol, separating the words with

a space.

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Nomenclature of Alcohols

•Compounds with two OH groups are called diols

or glycols.

•Compounds with three OH groups are called triols.

1,2-ethanediol
1,2-cyclopentanediol

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Interesting Alcohols
Common alcohols
•Methanol (CH3OH) is a useful as a solvent and
a starting material for plastics, but it is toxic due
to its oxidation in the liver.

•Ethanol (CH3CH2OH) is the alcohol present in

alcoholic beverages, and it is formed from the
fermentation of carbohydrate chains.

•2-Propanol [(CH3)2CHOH), isopropyl alcohol] is

the major component of rubbing alcohol, which is
used to sterilize skin and medical instruments.

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Interesting Alcohols
Common Diols and Triols

•Ethylene glycol (HOCH2CH2OH), a diol, is the major

component of antifreeze; it is sweet tasting but
extremely toxic.

•Glycerol [(HOCH2)2CHOH], a triol, is used in

lotions, liquid soap, and shaving cream; it is also
sweet tasting, but nontoxic, so it can be used
in food products.

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REACTIONS OF
ALCOHOLS
• THE reactivity of alcohols is mainly attributed to the -OH group.
• This functional group has an inherent acid character shown when the
hydrogen is released from the –OH bond.
• The case of removal is dependent upon the relative polarization of the
–OH bond.
• The –OH group may also be protonated at the oxygen , which
weakens the CO bond so that the whole group may be cleaved off as
water and subsequently replaced in the molecule.
CHROMIC ACID TEST

• PRIMARY and SECONDARY alcohols may be distinguished from

TERTIARY ALCOHOLS by the CHROMIC ACID test.
• Primary alcohols are oxidized to aldehydes, while
• Secondary alcohols are oxidized to ketones
• Tertiary alcohols do not react with chromic acid.
Chromic acid test

• Primary alcohol + CHROMIC ACID ALDEHYDE + CHROMIUM ION ( GREEN SOLUTION)

• Secondary alcohol + CHROMIC ACID KETONE + CHROMIUM ION ( GREEN SOLUTION)

• Tertiary alcohol + CHROMIC ACID no reaction

( because of the absence of an alpha hydrogen)
1. Oxidation: OXIDIZING AGENT
(CHROMIC ACID)
Oxidation results in an:
•increase in the number of C—O bonds
•decrease in the number of C—H bonds

The symbol [O] indicates an oxidation reagent

(commonly K2Cr2O7) has been added.
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Reactions of Alcohols
Oxidation
•Primary (1o) alcohols first oxidize to aldehydes
(RCHO), replacing 1 C—H with 1 C—O.
•Aldehydes are further oxidized to carboxylic
acids (RCOOH), replacing 1 C—H with 1 C—O.

1o alcohol aldehyde carboxylic acid

(ROH) (RCHO) (RCOOH)
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Reactions of Alcohols
Oxidation
•Secondary (2o) alcohols are oxidized to ketones
(R2CO).

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Reactions of Alcohols
Oxidation
•Tertiary (3o) alcohols have no H atoms on the C
with the OH group, so they are not oxidized.

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LUCAS TEST

• TO FURTHER distinguish the different classes of alcohols, LUCAS TEST

is employed.
• Tertiary alcohols react immediately to form an immiscible upper layer
of alkyl chloride.
• The alkyl chloride is insoluble in the medium and causes the solution
to become cloudy before it separates as a distinct layer.
• with Secondary alcohols the cloudiness appears after 5 minutes
• while primary alcohols do not react under these conditions
• TERTIARY ALCOHOL WHEN REACTS WITH LUCAS REAGENT (HCl & ZnCl2)
forming the insoluble tertiary butyl chloride in water

CH3 CH3
I I
CH3 –C- OH + HCl ZnCl2 CH3 –C- Cl + HOH
I I
CH3 CH3
Acrolein test
• The most important triol is glycerol . It is obtained as a by product
from the manufacture of soap. It is used as a moisturizing agent in
cosmetic formulation , in tobacco products and in foods.
• Glycerol is detected by the acrolein test.
• Glycerol undergoes dehydration when heated with KHSO4 to form
propenal which has a pungent odor or odor of burned fat.
• Please check equation in p. 64 of your lab manual.
Fermentation

• The most commonly known primary alcohol is ethyl alcohol.

• It is the alcohol present in all alcoholic beverages.
• Ethyl alcohol or ethanol is obtained from the fermentation of sugars
and starches.
• This reaction is catalyzed by the enzyme zymase which is found in
yeast.
• C6H12O6 ZYMASE CO2 + CH3 –CH2- OH
a. Task #1 Individual task
• 1. Give the structures & classifications (primary, sec. tert. diol, triol, aromatic…)
of the different alcohol test solutions
a. n-Butyl alcohol
b. Glycerol
c. Sec. butyl alcohol
d. Tert. Butyl alcohol
e. Benzyl alcohol
f. Methanol
g. Isopropyl alcohol
h. Ethyl alcohol
• 2. Give the composition/ reagents of the following tests for alcohol.
a. CHROMIC ACID TEST
b. Lucas test
c. Esterifications
d. Special test for Methyl alcohol
e. Iodoform test
f. Test for glycerol
g. Fermentation
Task #2 ( Group Task)

• 3. Give the schematic diagram for all the procedures of Expt. # 13

• 4. Give the principle behind the procedures for all the test for
Alcohols.
Task #3 (GROUP task):

Do an extensive research and Give the possible evidence of the

following test.
a. Chromic acid test - Group 1
b. Lucas test - Group 2
c. Esterification - Group 3
d. Special test for Methyl alcohol -Group 4
e. Iodoform test - Group 5
f. Test for glycerol - Group 6
g. Fermentation - Group 7
 Thank you Class
keep safe & God bless
you all

Dr. Mina