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 Kekul structure (named after August Kekul 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 )
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
HO 2C

ibuprofin

HO2C

CH3

O
CH2CNH

NH
lysergic acid

CH3
N

O
OH

OH
morphine

S
N

penicillin G CO H
2

- 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
NDesigner

OH

OH
morphine

O
OCH3
codeine

CH3

CH3

OH

OCH3
oxycodone
oxycontin (slow release)
percocet (w/ acetominophen)

O
OAc
heroin

OAc

Drugs

 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

CH3 O

H
O

CH3
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

acetyl salicylic acid

HO2C

(S)(+)ibuprofin

Fats and Fatty Acids

O
CH2

OCR
O

CH

OCR
O

CH2
OCR
a triglyceride

CO 2H
palmitic acid (a fatty acid)

R = n-C15H31

From Ergot Fungus

HO2C

CH3
N
H

(+) lysergic acid

NH

Functional Groups
link to Careys site

(CH3)2N
OH
C CH

H2NCHCNHCHCOCH3
HOCCH2
O

O
Mifepristone (RU-486)

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

NH

OH

O
O

OH

OH O O
O

Taxus brevifolia