PHA 034 ORGANIC

CHEMISTRY

ALCOHOLS AND
PHENOLS
PERIODICAL 3
WEEK 1
MODULE 18
LEARNING OUTCOMES
1. Know the physical properties of alcohols
2. Understand how alcohols are prepared
3. Learn the different reactions that alcohols can undergo
4. Enumerate qualitative tests for alcohols
5. Know some pharmaceutically important alcohols and their uses
6. Know the physical properties of phenol
7. Understand the preparation of phenols
8. understand the reactions that phenols undergo
9. Know some pharmaceutically important phenolic compounds
10. Determine the characteristics of an ideal antiseptic
ALCOHOLS
ALCOHOLS
R-OH (Hydroxyl)

Physical properties:
○ organic analogues of water
○ Highly polar
○ Hydroxyl group is hydrophilic, the alkyl/hydrocarbon group is
hydrophobic

Water solubility: Decreases as the number of carbons

increases
Boiling point: Increases as the number of carbons increases
PREPARATION
● Hydration of alkenes (addition of water)

● Catalytic hydrogenation or metal halide

reduction of aldehydes, ketones, carboxylic
acids

● Nucleophilic addition of organometallic

reagents to aldehydes, ketones, alkyl
halides, and esters
REACTIONS
DEHYDRATION - removal of water
Product: Alkenes

OXIDATION
Reagent: Potassium dichromate (K2Cr2O7)
Primary alcohol --> aldehyde --> carboxylic acid
Secondary alcohol --> ketone
Tertiary alcohol (no reaction)
QUALITATIVE TESTS FOR
ALCOHOLS
1. LUCAS TEST
Reagent: Zinc chloride in concentrated HCl
differentiates alcohols by forming an insoluble
layer

*Tertiary alcohols are the most reactive.

Primary alcohols need heat.
2. WILLIAMSON’S REAGENT
for synthesis of ethers

Most reactive: Methanol > Primary >

Secondary > Tertiary
 PHARMACEUTICALLY
IMPORTANT ALCOHOLS
METHANOL (CH3OH)
● “Wood alcohol”
● formerly obtained from destructive
distillation
● used to produce formaldehyde (starting
material for plastics)
Toxicity
Methanol ---> Formaldehyde --> Formic acid
(blindness due to metabolic acidosis)

Antidote: Ethanol
ETHANOL
“Grain alcohol” “Wine spirit”
“Spiritus vini rectificatus”

○ present in alcoholic beverages

○ obtained from fermentation of sugars and
starch
○ antiseptic (70% solution)
○ used as solvent in tinctures and other
alcoholic medicinal preparations
Ethanol metabolism
occurs in the liver

EtOH ---> Acetaldehyde --> Acetic acid

Acetic acid (causes liver damage)

ISOPROPYL ALCOHOL
“Rubbing alcohol”

● used in the production of acetone

● pharmaceutical solvent
ETHYLENE GLYCOL
● antifreeze
● brake fluids
● ink, paints
● pharmaceutical solvent
Ethylene glycol --> Oxalate (Oxalic acid) +
Calcium --> (hypocalcemia)

Calcium oxalate deposits - cause kidney

stones
PHENOLS
PHENOLS
hydroxyl group attached to an aromatic
hydrocarbon group

more acidic than alcohol

Physical Properties
● Have higher boiling points
● Susceptible to oxidation
PREPARATION
● Hydrolysis of diazonium salts

● Alkali fusion of sulfonates

REACTIONS
● ELECTROPHILIC SUBSTITUTION
● SALT FORMATION WITH ALKALI
● ETHER FORMATION
● ESTERIFICATION
● CARBONATION (Treatment with CO2)
Example: Phenol --> Salicylic acid
● REIMER-TIEMANN REACTION
treatment of a phenol with chloroform and aqueous
hydroxide to yield an ALDEHYDE
● REACTION WITH FORMALDEHYDE
PHARMACEUTICALLY
IMPORTANT PHENOLS
PHENOL (Carbolic acid)
○ disinfectant for surgical instruments
○ antiseptic for skin
○ starting material in the manufacture of aspirin,
detergents, dyes, herbicides, explosives

Bacteriostatic: 0.1%-1%
Bactericidal/Fungicidal: 1%-2%
Irritating and corrosive to tissues: 5%
CRESOL
LYSOL
○ colorless, but turns dark brown upon prolonged
exposure to light and air
○ commonly used as a surface disinfectant
○ less toxic than phenol
GLYCEROL
○ odorless, sweet liquid
○ used in the manufacture of certain plastics
○ solvent in liquid medications
○ ingredient in cosmetics formulation
○ vehicle for suppositories
○ When ingested, it attracts water into the intestines
and softens the stool, relieving constipation.
CHOLESTEROL
○ waxy, fat-like substance found in the cell
membrane
○ precursor for the synthesis of reproductive
hormones and bile acids
HEXYL RESORCINOL
● antiseptic and germicide
● commonly used in mouthwash
MENTHOL
● from Peppermint oil
● white, crystalline substance
GERANIOL
● From Rose oil
● commonly used in food, fragrance, and
cosmetic industry
GLUCOSE
● basic carbohydrate unit
● blood sugar
● found in fruits and honey
● major source of energy for cellular function
Characteristics of an IDEAL
ANTISEPTIC
● Low surface tension
● Non-irritating to tissue and non-allergenic
● must retain its activity in the presence of
body fluids
● Has rapid and sustained action against
microorganisms