Alcohols Pharm 122L

Prepared by: Victoria Dawn A. Aliguyon, RPh

01. 02.
Nomenclature Physical Properties

03. 04.
Chemical Properties Application
 C - OH
CnH2n+1OH

� Hydroxyl vs. Hydroxide

- OH vs OH - OH
Structural Formula

Line Angle Structural Formula

01.
Nomenclature
A. Common name: alkyl group (number of
carbons) followed by the word alcohol
The prefix “iso” is used in branching form
 Nomenclature
B. IUPAC name
1. Name the longest carbon chain to which the hydroxyl group is attached.
The chain name is obtained by dropping the final -e from the alkane
name and adding the suffix -ol.
2. Number the chain starting at the end nearest the hydroxyl group, and
use the appropriate number to indicate the position of the —OH group. 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.
3. Name and locate any other substituents present.
4. In alcohols where the —OH group is attached to a carbon atom in a ring,
the hydroxyl group is assumed to be on carbon 1.
 Nomenclature
B. IUPAC name: Examples
1. Monohydroxylic Alcohol

2. Polyhydroxylic Alcohol
02.
Physical
Properties
Physical Properties
• Liquid, colorless, odorless
Boiling point:
• ↑ increase of carbon masses. = ↑ BP
• ↓ BP = ↑ in branching in aliphatic carbon
chains the Van der Waals forces
decreases with a decrease in surface
area.
Solubility:
• Governed by Hydroxyl group
• 1 to 3 carbons atoms:
completely soluble in water
• ↑ chain length=↓solubility
(hydrocarbons)
Acidic:
• Due to the polarity of –OH bond
• reacts w/ Na, K, etc. to form
alkoxide
03.
Chemical
Properties
Chemical Properties
Summary of Chemical
Reactions Involving
Alcohols
 Chemical Properties

Combustion Halogenation Dehydration

Chemical Properties

Combustion
C2H5OH + 3O2 → 2CO2 + 3H2O
 Chemical Properties

Halogenation
CH3CH2OH + HBr → CH3CH2Br + H2O
 Chemical Properties

Dehydration
1. Intramolecular dehydration: H2O components are removed.
2. Intermolecular dehydration: there is more than one neighboring carbon
atom from which hydrogen loss can occur which can result to isomeric
alkenes .
Chemical Properties

Dehydration
Chemical Properties

Dehydration
� Alcohol also has various classes and
they differ in chemical properties.

Primary Secondary Tertiary

 Chemical Properties

Oxidation Lucas Test

 Chemical Properties

Oxidation
O.A:
• KMnO4
• K2Cr2O7
• H2CrO4
Lucas Test
Preparation of Alcohol
Did You Know This?
03.
Pharmaceutical
Applications of
Alcohol
 Pharmaceutical Applications of Alcohol
Ethyl Alcohol • An advantage of ethanol is that growth of
microorganisms does not occur in solutions containing
“Drinking alcohol” and “Grain Alcohol”
alcohol in a reasonable concentration.
Uses:
• starting point in the manufacture of many important compounds, like ether, chloroform
• solvent to cleanse the skin splashed with phenol
• a concentration of 25% it is employed for bathing the skin for the purpose of cooling and
reducing fevers
• a concentration of 50% it is used to prevent sweating in astringent and anhidrotic lotions
• cleanse and harden the skin and is helpful in preventing bedsores in bedridden patients •a
concentration of 60 to 90% it is germicidal
• optimum concentration (70% by weight) it is a good antiseptic for the skin and also for
instruments
• in high concentrations it is a rubefacient and an ingredient of many liniments
 ● marketed as in 70%
concentration as antiseptic
Ethyl Alchol ● employed in some liniment
•AKA “Rubbing Alcohol, 2- and lotion formulations and
propan-1-ol” cannot be taken internally
● recognized as a rubefacient,
although it is used more
widely as an antiseptic
 Pharmaceutical Applications of Alcohol
Glycerin
“Glycerol, Propane-1,2,3 triol”

• humectant in keeping substances moist

• in pure anhydrous form, it is used in the eye
to reduce corneal edema and to facilitate
ophthalmoscopic examination
• in the form of suppositories, promotes
defecation by stimulating the rectal
mucosa
• it also acts to lubricate and soften
inspissated fecal material.
Pharmaceutical Applications of Alcohol
Propylene Glycol
“Propane-1,2-diol”

• solvent for drugs

• preservative in a variety of liquid
pharmaceutical formulations,
including parenteral
• carrier for emulsifiers and as a
vehicle for flavors