Functional Groups
– Alkenes
• Ethene (ethylene) is a major industrial feedstock
– Used in the production of ethanol, ethylene oxide and the
polymer polyethylene
• Propene (propylene) is also very important in industry
– Molecular formula C3H6
– Used to make the polymer polypropylene and is the starting
material for acetone
• Many alkenes occur naturally
2
– Alkynes
• Ethyne (acetylene) is used in welding torches
because it burns at high temperature
• Many alkynes are of biological interest
– Capillin is an antifungal agent found naturally
– Dactylyne is a marine natural product
– Ethinyl estradiol is a synthetic estrogen used in oral
contraceptives
– Benzene: A Representative Hydrocarbon
• Benzene is the prototypical aromatic compound
– The Kekulé structure (named after August Kekulé who formulated it)
is a six-membered ring with alternating double and single bonds
• Benzene does not actually have discreet single and double
carbon-carbon bonds
– All carbon-carbon bonds are exactly equal in length (1.38 Å)
– This is between the length of a carbon-carbon single bond and a
carbon-carbon double bond
• Resonance theory explains this by suggesting there are two
resonance hybrids that contribute equally to the real structure
– The real structure is often depicted as a hexagon with a circle in the
middle
Some Well-known Aromatic Compounds
CO 2H O
OCCH3
acetyl salicylic acid
ibuprofin
HO 2C
N
HO 2C
CH3
O
CH2CNH
NH
CH3
N
lysergic acid
O
OH
OH
morphine
S
N
penicillin G
CO 2H
- Alkyl Halides
In alkyl halides, a halogen (F, Cl, Br, I)
replaces the hydrogen of an alkane
– Alcohols
• In alcohols the hydrogen of the alkane is replaced
by the hydroxyl (-OH) group
– An alcohol can be viewed as either a hydroxyl derivative
of an alkane or an alkyl derivative of water
• Alcohols are also classified according to the carbon
the hydroxyl is directly attached to
Chapter 2
Some Alcohols
CH3CH2OH
ethanol
HO
HO
OH
OH
CHCH2NH2
CHCHNHCH3
adrenaline
CH3
pseudephidrine
OH
HOCH2CHCH2OH
glycerol
cholesterol
HO
Alcohols are Found in Many Natural Products
HO
N CH3
O
H
HO
Morphine
most abundant of opium's alkaloids
CH3
CH3
N
N
O
OH
OH
morphine
O
OH
OCH3
codeine
CH3
N
O
Designer Drugs
CH3
N
O
OCH3
oxycodone
oxycontin (slow release)
percocet (w/ acetominophen)
O
OAc
heroin
OAc
– Ethers
• Ethers have the general formula R-O-R or R-O-R’
where R’ is different from R
– These can be considered organic derivatives of water in
which both hydrogens are replaced by organic groups
– The bond angle at oxygen is close to the tetrahedral
angle
– Amines
• Amines are organic derivatives of ammonia
– They are classified according to how many alkyl groups
replace the hydrogens of ammonia
– This is a different classification scheme than that used in
alcohols
– Aldehydes and Ketones
• Both contain the carbonyl group
• Aldehydes have one carbon attached to the carbonyl group
• Ketones have two organic groups attached to the carbonyl
group
• The carbonyl carbon is sp2 hybridized
– It is trigonal planar and has bond angle about 120o
Adrogenic/Anabolic Steroids
CH3 OH
CH3
H
CH3 O
H
CH3
H
O
H
H
H
O
Testosterone
Androstenedione
– Carboxylic Acids, Esters and Amides
• All these groups contain a carbonyl group bonded
to an oxygen or nitrogen
• Carboxylic Acids
– Contain the carboxyl (carbonyl + hydroxyl) group
• Esters
– A carbonyl group is bonded to an alkoxyl (OR’) group
Analgesics
CO2H O
OCCH3
(S)(+)ibuprofin
acetyl salicylic acid
HO2C
Fats and Fatty Acids
CO2H
palmitic acid (a fatty acid)
O
CH2
OCR
O
CH
OCR
O
CH2
OCR
a triglyceride
R = n-C 15H31
From Ergot Fungus
HO2C
CH3
N
H
(+) lysergic acid
NH
Functional Groups
link to Carey’s site
(CH3)2N
O
OH
C CH
H2NCHCNHCHCOCH3
HOCCH2
O
O
Mifepristone (RU-486)
O
Aspartame
CH2
• Amide
– A carbonyl group is bonded to a nitrogen derived from
ammonia or an amine
– Nitriles
• An alkyl group is attached to a carbon triply bonded
to a nitrogen
– This functional group is called a cyano group
Chapter 2
Summary of Important Families of Organic
Compounds
Summary (cont.)
From the Bark of the
Pacific Yew Tree
O
O
O
NH
OH
O
O
O
OH
O
OH O O
O
Taxus brevifolia
O