Organic Chemistry I
Review of Functional Groups
I.
Functional Groups With Carbon-Carbon Multiple Bonds
Alkenes and aromatic compounds contain sp2 hybridized carbon atoms and have pi bonds associated with them. Alkenes contain
only double bond. Aromatic compounds can contain both double bonds and triple bonds. Alkynes contain only triple bonds an
can be classified as terminal or internal. Enynes are organic molecules that contain both double and triple bonds.
Alkenes
Alkynes
Alkene
Diene
Triene
Arenes (Aromatic Compounds)
Enynes
N
Benzene
Naphthalene
Pyridine
Example drug molecules:
O
O
O
O
O
HN
O
OH
O
O
CH3
Pyrethrin II
Compound found in marigolds
Potent Insecticide
Causes skin allegeries in some people
Dynemicin A
Antibacterial and anticancer activity
II. Functional Group with Carbon Singly Bonded To An Electronegative Element
A. Alkyl Halides: Alkyl halides contain a halogen atom bonded to an sp3 carbon. They may be 1°, 2° or 3° depending on
the substitution of the carbon atom bonded to the halogen. Vinyl halides are organic compounds which contain a
halogen bonded to the sp2 carbon of an alkene. Aryl halides are organic compounds which contain a halogen bonded to
the sp2 carbon of an aromatic system.
Alkyl Halides
Cl
C
H
Cl
C
CH 3
CH 3
CH 3
1°
CH 3
H
H
2°
Cl
C
Cl
CH 3
Cl
CH 3
Vinyl halide
3°
1
Aryl Halide
Organic Chemistry I
Review of Functional Groups
B. Alcohols: Alcohols contain an -OH group bonded to an sp3 carbon. Alcohols are designated as primary (1°), secondary
(2°) or tertiary (3°) depending on the substitution of the carbon atom to which the hydroxyl group is bonded.
secondary alcohol
OH
C
C
C
H
OH
C
C
H
H
OH
H
C
OH
H
H
C
C
teriary alcohol
secondary alcohol
HO
C
primary alcohol
phenol
C. Ethers: Ethers are organic compounds which contain an oxygen bonded to two carbon atoms. The carbons may be sp,
sp2 or sp3 hybridized.
CH3
3
sp
C
O
C
C
O
O
N
sp2
C
Cl
ether
CH3
D. Amines: Amines are organic compounds which contain a nitrogen atom bonded to one or more sp3 carbons. Amines
may be designated as primary, secondary or tertiary depending on the number of carbon atoms the N atom of the amine
is bonded to.
tertiary amine
N
O
N
C
C
C
NH2
NH
C
N
C
N
Cl
F
C
tertiary
secondary
X
N
C
C
primary
C
Flurazepam
quarternary salt
E. Thiols: Thiols are organic compounds which contain an -SH group bonded to an sp3 carbons. Thiols are related
structurally to alcohols.
aromatic
sp
sp
3
SH
sp2
C
SH
C
SH
C
2
SH
Organic Chemistry I
Review of Functional Groups
F. Sulfides: Sulfides are organic compounds which contain a sulfur atom bonded to two carbon atoms. The carbons may
be sp, sp2 or sp3. Sulfides are structurally related to ethers
sp3
C
S
C
C
S
sp2
C
.
Example Drug Molecules:
H
CH 3
F 3C
N
O
S
CH 3
HO
HO
Br
O
CH 3 O
O
S
N
N
H
O
Letosteine
(Mucolytic)
O
O
Oxycodone
III. Functional Groups with A Carbon-Oxygen Double Bond
A. Aldehydes: Aldehydes contain a carbon oxygen double bond. The carbon atom of the carbonyl group is also bonded to one
hydrogen and one carbon atom
O
O
C
C
H
H
B. Ketones: Ketones contain a carbon oxygen double bond. The carbon atom of the carbonyl is also bonded to two other
carbon atoms. Ketones may be acyclic or cyclic.
CH3
CH3
O
O
O
Acyclic
Testosterone
Cyclic
ketone
3
OH
Organic Chemistry I
Review of Functional Groups
C. Carboxylic Acids: Carboxylic acids contain a carbonyl group. The carbon atom of the carbonyl group is bonded to another
carbon atom and a hydroxyl group.
carboxylic acid
O
O
F
OH
O
O
OH
C
HN
OH
C
N
N
Ciprofloxacin
(antibiotic)
D. Esters: contain a carbonyl group. The carbon atom of the carbonyl group is bonded to another carbon atom and an ether type
oxygen, i.e., an oxygen bonded to another carbon. Esters are considered to be derivatives of carboxylic acids. Cyclic esters
are called lactones.
O
H3C
O
O
O
esters
N
O
O
OCH3
O
CH3
O
O
Acyclic ester
Cyclic ester
Cocaine
Acyclic ester
E. Amides: contain a carbonyl group. The carbon atom of the carbonyl group is bonded to another carbon atom and a nitrogen
atom. Amides can be primary secondary or tertiary. The nitrogen atom of the primary amide is bonded to the carbonyl
carbon and two hydrogens. The nitrogen atom of a secondary amide is bonded to the carbonyl carbon, one hydrogen and
another carbon. The nitrogen atom of a tertiary amide is bonded to the carbonyl carbon and two other carbons. Cyclic amides
are called lactams. Amides are derivatives of carboxylic acids.
O
O
O
NH
Primary
2
N
H
Secondary
O
O
HO
O
O
NH
N
N
N
H
Tertiary
O
Lactam
Enalapril
(antihypertensive)
amide
F. Acid Chlorides
Acid chlorides are organic compounds which contain a carbonyl group bonded to a chlorine atom. Other halogens may also
be bonded to carbonyl groups. These compounds are acid bromides, acid chlorides...Acid chlorides are derivatives of
carboxylic acids.
O
O
Cl
C
4
C
Cl
Organic Chemistry I
Review of Functional Groups
G. Anhydrides
Anhydrides are organic compounds which contain two carbonyl groups. The carbonyl groups are separated from each other
by an oxygen atom. Anhydrides may be acyclic or cyclic and are derivatives of carboxylic acids.
O
O
O
O
O
O
IV. Hetereocycles and Biologically Important Functional Groups
Nitrogen Containing Functional Groups &Heterocycles
H
N
N
N
H
N
H
Pyrrolidine
Pyrrole
N
N
Pyridine
Pyrazole
N
Quinoline
Isoquinoline
NH2
O
N
H
O
Cytosine
N
H
N
H
Indole
O
Uracil
(RNA only)
H3 C
N O
H
Thymine
(DNA only)
N
H
Nitromethane
N
N
H
N
N
Adenine
OH
N
N
H
5
N
N
NH2
Guanine
Purine Bases
Pyrimidine Bases
Urea
Purine
NH2
NH
NH2
CH3NO2
N
O
NH
N
H2 N
N
N
N
O
N
H
Piperazine
Pyrazine
H
Succinimide
H
N
N
Pyrimidine
N
O
N
N
N
H
Piperidine
O
N
N
H
Imidazole