PHA 034 ORGANIC

CHEMISTRY

ETHERS

PERIODICAL 3
WEEK 2
MODULE 19
LEARNING OUTCOMES
1. Define ethers and their physical properties
2. Know how ethers are prepared
3. Know the reactions that ethers undergo
4. Enumerate some pharmaceutically important ethers
5. Define thiols and thioethers
6. Determine their physical properties
7. Determine how they are prepared
8. Enumerate some pharmaceuticallyl important thiols and
thioethers
ETHERS
R-O-R
also known as organic oxides

○ Organic relatives of water, where alkyl groups

replace both hydrogen atoms
○ Two hydrocarbons bonded to an oxygen atom
○ Commonly used as solvents in organic
reactions
PREPARATION
● WILLIAMSON ETHER SYNTHESIS
● ACID-CATALYZED ADDITION OF
ALCOHOLS TO ALKENES
● OXIDATION OF ETHYLENE
REACTION
● Simple ethers are unreactive towards
bases, oxidizing agents, and reducing
agent.
● Nucleophilic substitution to yield alkyl
halides
● Nucleophilic substitution with acids and
bases to yield alcohols
PHARMACEUTICALLY
IMPORTANT ETHERS
 solvent for waxes and fats solvent for varnishes and
formerly used as inhalation laboratory organic synthesis;
anesthetic highly flammable

SIMPLEST AND MOST COMMON ETHERS

ANISOLE
● used in perfumes and cosmetics
POLYETHYLENE GLYCOL
● PEG
● used in pharmaceuticals as surfactant,
emulsifiers, humectant
● has a laxative effect
ETHYLENE OXIDE
● Gas sterilant
● fumigant for textiles and grains
MONOBENZONE
● depigmenting agent in cases of excessive
melanin production
● used in whitening preparations
EUGENOL
● From Clove oil
● used to treat toothaches
● used in dentistry as temporary fillings when
mixed with ZnO
NAPROXEN
● NSAID (Non steroidal anti-inflammatory
drug)
● for mild pain due to headaches, muscle
aches, arthritis, menstrual pain, backaches,
toothaches

Flanax®
Skelan®
 PHA 034 ORGANIC
CHEMISTRY

THIOLS AND THIOETHERS

PERIODICAL 3
WEEK 2
MODULE 20
THIOLS [R-SH]
also known as MERCAPTANS
sulfur analogs of alcohol
PHYSICAL PROPERTIES
● lower boiling points than alcohols
● less polar than alcohols
● more acidic than alcohols
PREPARATION
SN2 Reaction of alkyl halide and sodium
hydrosulfide
REACTIONS
● OXIDATION
yields disulfides
THIOETHERS [R-S-R]
● also called SULFIDES
● sulfur analogs of ethers
PREPARATION
SN2 REACTION
Treatment of thiol with base
 PHARMACEUTICALLY
IMPORTANT THIOLS AND
THIOETHERS
DISULFIRAM
● treatment of chronic alcoholism
● causes unpleasant effects when taken with
alcohol
SULFONAMIDE
● basis of sulfa drugs
● synthetic antimicrobial drugs used for
treatment of bacterial infections
QUETIAPINE
● Antipsychotic durg
● used for schizophrenia, acute manic
episodes, anxiety disorders
● also used as treatment for major
depressive disorder