ALCOHOLS

and
PHENOLS
ALCOHOLS
• Alcohol is any compound in which a hydroxyl functional group (-
OH) is bound to a carbon atom.

There are three classes (types) of alcohols:

• Primary- (1°) RCH2OH alcohol, the carbon which carries the -OH
group is only attached to one alkyl group.

• Secondary- (2°) R2CHOH alcohol, the carbon with the -OH group
attached is joined directly to two alkyl groups.

• Tertiary- (3°) R3COH alcohol, the carbon atom holding the

-OH group is attached directly to three alkyl groups.
PROPERTIES OF
ALCOHOLS
 The Boiling Point of Alcohols

From the graph we can see that the boiling point of an

alcohol is always much higher than the boiling point of the
corresponding alkane with the same hydrocarbon chain.
The boiling point of alcohols also increase as the length of
hydrocarbon chain increases.
• The reason why alcohols have a higher boiling point
than alkanes is because the intermolecular forces of
alcohols are hydrogen bonds, unlike alkanes with
van der Waals forces as their intermolecular forces.
 The Solubility 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. As the length of the
hydrocarbon chain increases, the solubility in
water decreases.
 The Solubility of Alcohols

With four carbon in the hydrocarbon chain

and higher, the decrease in solubility
becomes visible as the mixture forms two
immiscible layers of liquid. The reason why
the solubility decreases as the length of
hydrocarbon chain increases is because it is
requires more energy to overcome the
hydrogen bonds between the alcohol
molecules as the molecules are more tightly
packed together as the size and mass
increases.
 The Acidity of Alcohols

Alcohols react with active metals such as sodium,

potassium etc. and form the corresponding alkoxide.
These reactions of alcohols are indicative of their acidic
nature. The acidic nature of alcohol is due to the
polarity of –OH bond. The acidity of alcohols decreases
when an electron donating group is attached to the
hydroxyl group. This is due to the fact that it increases
the electron density of the oxygen atom. Thus, primary
alcohols are generally more acidic.
 Chemical
Reaction of
Alcohols
Chemical reactions in alcohols occur mainly at the
functional group, but some involve hydrogen atoms
attached to the oh-bearing carbon atom or to an adjacent
carbon atom.

Of the three major kinds of alcohol reactions;

-Dehydration
-Oxidation
-Esterification
 DEHYDRATION
Dehydration can be performed in a 3 step
mechanism
• Formation of protonated alcohol
• Formation of carbocation
• Formation of alkene
 Formation of Protonated Alcohol

• In this particular step, the alcohol is reacted upon

by a protic acid. Due to the single pair present on
the oxygen atom, it acts as a lewis base. This step
is easily and quickly reversible.
Formation of Carbocation
• In this step, the C-O bond breaks which generate a
carbocation. This is the slowest step in the mechanism
of dehydration of alcohol. Therefore, the formation of
carbocation is said to be the rate determining step.
Formation of Alkene

• This is the final step in the dehydration of alcohols. In

this step, the proton generated is eliminated with the
help of a base. The carbon atom neighboring to the
carbocation breaks the present C-H bond to form C=C.
Therefore, alkene is formed.
 Oxidation
• The oxidation of alcohols is an important
reaction in organic chemistry.
• Primary alcohols can be oxidized to form
aldehydes and carboxylic acids;
• Secondary alcohols can be oxidized to give
ketones.
• Tertiary alcohols, in contrast, cannot be
oxidized without breaking the molecule's C–C
bonds.
 1. Primary alcohols
can be oxidized to aldehydes or
further to carboxylic acids.
 2. Secondary alcohols
can be oxidized to ketones but no
further:
3. Tertiary alcohols
cannot be oxidized
(no carbinol C-H)
 Esterification
• Esterification is the process of combining an
organic acid (RCOOH) with an alcohol
(ROH) to form an ester (RCOOR) and water;
or a chemical reaction resulting in the
formation of at least one ester product.
Ester is obtained by an esterification
reaction of an alcohol and a carboxylic acid.
EXAMPLES
 ALCOHOL
 an alcohol exists when a hydroxy group, a pair of
oxygen and hydrogen atoms, replaces the hydrogen
atom in a hydrocarbon.
 Alcohols bind with other atoms to create secondary
alcohols. These secondary alcohols are the three
types of alcohol that humans use every day:
methanol, isopropanol, and ethanol.
 ETHANOL
 Ethanol (or ethyl alcohol) is the type of alcohol that over two billion
people drink every day.
 produced by the fermentation of yeast, sugars, and starches.
 ethanol also has harmful effects on the body. The human liver can
metabolize ethanol, but only in limited quantities.
 Ethanol is toxic, so it damages organs over time.
 Ethanol also inhibits the central nervous system,  thereby
impairing coordination and judgment.
 Additionally, binge drinking and other forms of alcohol abuse can
cause a person to develop debilitating alcohol addiction.
 METHANOL
 Methanol (or methyl alcohol) is a component in fuel
for cars and boats. It’s also used to manufacture
antifreeze, paint remover, windshield wiper fluid, and
many other products.
 ISOPROPANOL
 Isopropanol (or isopropyl alcohol) is the chemical
name for rubbing alcohol, which we use for cleaning
and disinfecting. Both methanol and isopropanol are
poisonous to humans because our bodies
metabolize them as toxic substances which cause
liver failure. Drinking even a small amount of
methanol or rubbing alcohol can be fatal.
Distilled and
Undistilled
Alcohol
 Distilled Alcohol

• These types of beverages are prepared by

the distillation of without distilled beverage
and the amounts of alcohol vary from
(40-55) % as below
Distilled Alcohol
 Undistilled Alcohol

• These types of beverage are prepared by the fermentation of

fruits juices or food grains and on filtration of fermented
liquid and some wanted flavour; colour and perfumes are
accessed (intermixed). The amounts of alcohol vary from (3-
15) % as below;
Undistilled Alcohol
C6H5OH or C6H6O

PHENOLS
PROPERTIES OF
PHENOLS
 PHYSICAL PROPERTIES OF PHENOLS
• Other name: Cresols
• Colorless, crystalline, poisonous solid with phenolic
odor
• Causes blisters on skin
• Used as disinfectants and in washrooms
 Chemical Properties of Phenol

1. Boiling Point of Phenols

Phenols generally have higher boiling points in
comparison to other hydrocarbons having
equal molecular masses. This is due to the
presence of intermolecular hydrogen bonding
between hydroxyl groups of phenol molecules.
• In general, the boiling point of phenols increases with
an increase in the number of carbon atoms.
• 181.7 °C
2. Solubility of Phenols
- The solubility of phenol in water is governed by the
hydroxyl group present.
- The hydroxyl group in phenol is involved in the
formation of intermolecular hydrogen bonding.
- Thus, hydrogen bonds are formed between water and
phenol molecules which make phenol soluble in water.
- However, the aryl group attached to the hydroxyl
group is hydrophobic in nature.
- Thus, the solubility of phenol decreases with the
increase in the size of the aryl group or alkyl group.
Completely soluble 0 to 65 °C; above 65.3 °C
phenol and water
 3. Acidity of Phenols

• the acidity of phenols increases in the

presence of the electron-withdrawing group.
This is due to the stability of the phenoxide ion
generated. The acidity of phenols further
increases if these groups are attached at
ortho and para positions.
This is due to the fact that the negative charge in
phenoxide ion is mainly delocalized at ortho and para
positions of the attached benzene ring.

On the other hand, the acidity of phenols decreases in

the presence of electron-donating groups as they
prohibit the formation of phenoxide ion.
 Chemical
Reaction of
Phenols
 Chemically, phenols are weakly acidic compounds
 The Hydrogen dissociates to a small degree from the
hydroxyl radical to act as an acid as shown below.

 Since Phenols are weak acids, they will form salts with
inorganic bases
 Phenols with two hydroxyl groups also undergo oxidation
reaction
 Reaction of Phenols
• Phenols react in a wide variety of ways.
 Reaction with bromine Water
 Nitration
 Reactions with Aqueous iron (III) chloride
 Esterification
 Formation of Ether
 Reaction with bromine Water

 Phenols form a white precipitate of 2,4,6-

tribromophenol immediately when it is treated
with bromine water at room temperature
 The reddish brown color of bromine disappears
and white fumes of hydrogen bromine are
released
 Nitration

 Nitration of phenol can be carried out at room

temperature by using dilute nitric acid

 The product is a mixture of 2-nitrophenol and 4

nitrophenol
 Reactions with Aqueous iron (III) chloride

 Phenol produces a purple coloration when treated with

natural aqueous solution of iron (III) chloride at room
temperature
 Esterification

 Phenol does not form ester with carboxylic

acids, but in the presence of an alkali such
as NaOH, the phenoxide ion which can act
as a nucleophile attacks the electrophilic
acyl group, RCO-, from acyl chloride

 The first step is the dissolution of phenol in

aqueous sodium hydroxide to form a
solution of sodium phenoxide

 Addition of a little liquid benzoyl chloride

gives a white precipitate of insoluble ester
immediately
 Formation of Ether
 When a alkane is added to a solution of phenol in an
alkali, the halogen atom is replaced by a phenoxide
ion in a nucleophilic substitution reaction

 The product is an aromatic ether

 When phenol react with sodium hydroxide and then

react ethylchloride and form ether
EXAMPLES
 Phenol is used for:
Phenols are widely used in household products and
as intermediates for industrial synthesis.

FOR EXAMPLE:

MOUTHWASH ANTISEPTIC DISINFECTANT

 -Examples of phenolics compounds
commonly present in foods: phenols (Ferulic
acid, Gallic acid) biphenols (resveratrol), and
polyphenols(tannic acid)

phenols Biphenols polyphenols

FERULIC ACID

RESVERATROL

GALLIC ACID

TANNIC ACID
Moreene Viane Kaye Aguilar
Efrelyn Lagmay
Jill Dagandanan
Laica Preza
Raina Gironella
Christine Mangasil

BSPHARMA1