ORGANIC

CHEMISTRY
After going through this module, you are expected
to:

1. define functional group;

2. describe the different functional groups;
3. identify the functional groups in organic compounds;
4. define isomerism;
5. name and define different kinds of structural
isomerism;
6. identify molecules that exhibit structural isomerism.
Organic Chemistry
Organic chemistry is the study of carbon compounds
except CO, CO2, HCO3-, CO32-, CN-, and C4-
compounds.
The word “organic” was originally used by
eighteenth-century chemists to describe
substances obtained from living sources such as
plants and animals.
 HISTORY
Friedrich Wohler, 1828
 PROPERTIES OF CARBON
1. Carbon is tetravalent forming 4 bonds
with itself and other elements
(heteroatoms) such as HONSPX
2. Carbon has the ability to form single,
double, and triple bonds (linear,
branched or cyclic)
7 single bonds 4 single bonds 2 single bonds
1 C-C bond 1 double bond 1 triple bond

6 C-H bonds 1 C=C bond 1 C≡C bond

4 C-H bonds 2 C-H bonds
Bond Length and Strength
 PROPERTIES OF CARBON
3. Organic molecules exhibit structural
isomerism and stereoisomerism
ISOMERISM
is a phenomenon in which more than one
compound have the same formula but
have different chemical structures.

CONSTITUTIONAL ISOMERISM
STEREOISOMERISM
CONSTITUTIONAL ISOMERISM
where compounds have different
connections of atoms.
STEREOISOMERISM
compounds have different spatial
arrangement of atoms.
 PROPERTIES OF CARBON
Lewis Structures
 PROPERTIES OF CARBON
Formal Charges
DRAWING STRUCTURES
Orbitals: s & p
 Hybridization
Combination of two or more AOs to form
the same number of Hos, each having
the same shape and energy
 Hybridization
Combination of two or more AOs to form the same
number of Hos, each having the same shape and
energy
sp3 hybridization of C
sp3 hybridization of C
sp2 hybridization of C
sp hybridization of C
Practice Problem:
FUNCTIONAL GROUP
A functional group is a group of atoms that is largely
responsible for the chemical behavior of the parent
molecule.
1. Hydrocarbons
2. Groups containing Halogens
3. Groups containing Oxygen
4. Groups containing Nitrogen
Functional Groups
I. Hydrocarbons
are organic compounds composed of
carbon-hydrogen chain.
1.Alkanes
are single-bonded aliphatic hydrocarbons.

They have a general formula of

CnH2n+2.

Their names end with -ane.

Example:
Give the (a) Structural formula, (b) Condensed
structural formula, (c) Lewis, and (d) line structures
of butane.
PHYSICAL PROPERTIES
PHYSICAL PROPERTIES
PHYSICAL PROPERTIES
Classification of C and H
IUPAC System of
Nomenclature
Origin of Parent Chain:
Alkanes
Alkyl groups
Name this alkane

1 2 3

propane
Name this alkane

1 2 3 4 5

pentane
Isomers of C5H12

Chain Isomers
Chain Isomerism
isomerism in which 2 or more compounds
have the same number of atoms and
functional groups but have different
arrangements of carbon skeleton in the
parent chain or in the side chains.
 Name this alkane

2 4 6 8
1
3 5 7

octane
 Name this alkane

2 4 6 8
1
3 5 7

2- methyl octane
 Name this alkane

2 4 6 8
1
3 5 7

2,2- dimethyl octane

 Name this alkane

2 4 6 8
1
3 5 7

2,2,6- trimethyl octane

 Name this alkane

2 4 6 8
8 7 6 5 4 3 2 1
1
3 5 7
6-ethyl-2,2-dimethyl octane
3-ethyl-7,7-dimethyl octane
 Note:

When assigning numbers, find the

substituents that is/are found in the
terminal carbon in the parent chain.
Name this alkane
 2,3-dimethyl -4-sec-butylheptane
1 2 3 4 5 6 7

methyl sec-butyl

Name this alkane

 2,3,5-trimethyl-4-propylheptane
1 2 3 4

5
propyl
6
methyl
7

Name this alkane

 Name this alkane

2,3-dimethyl-4-sec-butylheptane
2,3,5-trimethyl-4-propylheptane
Practice Problem
2. Cycloalkanes
are single-bonded cyclic hydrocarbons.

They have a general formula of CnH2n.

Their names start with cyclo- and end

with - ane.
Cyclopropane (C3H6)
 1-ethyl-2-methylcyclohexane

ethyl
1
methyl
6
2

3 5
4
Name this cycloalkane
Practice Problem
3. Alkenes
are double-bonded aliphatic/cyclic
hydrocarbons.

They have a general formula of CnH2n.

Their names and end with - ene.

 Lycopene

3-ethyl-2-methylcyclohexene
Geometric isomerism
Same number of atoms but different orientation
of atoms in space.

same opposite
4. Alkynes
are triple-bonded hydrocarbons.

They have a general formula of CnH2n-2.

Their names and end with - yne.

a. ethyne c. but-1-yne e. 1-phenylhept-1,3,5-triyne

b. prop-1-yne d. but-2-yne f. cycloheptyne

4. Aromatics
contain a planar unsaturated ring of atoms
that is stabilized by an interaction of the bonds
forming the ring.

Benzene as substituent = phenyl-.

II. Haloalkanes
These (symbolized as RX (R-alkyl groups and
X-any halogen eg. F, Cl, Br, I) are organic
compounds that contain Group VIIA nonmetal
elements.
-F (fluoro) -Br (bromo)

-Cl (chloro) -I (iodo)

Name this haloalkane
chloro

2 4
1

2-chlorobutane
 Name this haloalkane
chloro methyl
1

bromo 2
5

3 4

2-bromo-1-chloro-1-methylcyclopentane
III. Groups Containing Oxygen

Compounds that contain C-O bonds each

possess differing reactivity based upon the
location and hybridization of the C-O bond.
A.Alcohols
Alcohols are (symbolized as ROH) composed
of hydroxyl (-OH) group attached to parent
chain hydrocarbons.
The hydroxyl group replaces the hydrogen
from the main alkane chain.
Their names end with -ol.
As substituent = hydroxy-.
 Wood Spirit/Alcohol
Simplest alcohol

IUPAC Name: Methanol

 Commercially important alcohols

ethanol 2-propanol ethane-1,2-diol

ethyl alcohol Isopropyl alcohol Ethylene glycol

disinfectants Raw material for

polyesters and
antifreeze formulations
 Name this alcohol
hydroxyl/
5 3 1 alcohol

4 2

1-pentanol pentan-1-ol pentanol

Isomers of Pentanol

Positional Isomerism
Positional Isomerism
isomerism in which 2 or more compounds
have the same number of atoms and
functional groups but differ in the
arrangement of functional groups in the
parent carbon chain.
B. Ketones
Ketones are (symbolized as RCOR’)
composed of a carbonyl group (carbon -
oxygen double bond) attached to 2 alkyl
groups (R and R’).

Their names end with -one.

As substituent = oxo-.
 Propanone/Propan-2-one
Simplest ketone

Common name: Acetone

 Name this ketone

methyl

5 4 3 2 1

2,4-dimethyl pentan-3-one
Diones - 2 keto groups
 Isomers of C4H8O

2-butanone but-2-en-2-ol

Keto-enol tautomers
Tautomerism
isomerism in which 2 compounds differ only
in the position of the protons and
electrons but carbon skeleton of the
compound is unchanged.
C. Aldehydes
Symbolized as RCHO, aldehydes are
composed of a carbonyl group attached to
alkyl group (R) and H.

Their names end with -al.

As substituent = formyl-.
 Methanal / Formaldehyde
Simplest aldehyde

Commercial Name: Formalin (aq)

 Name this aldehyde
hydroxy

methyl

4 3 2 1

4-hydroxy -3-methyl butanal

D. Carboxylic acids
These (symbolized as RCOOH) are
composed of carboxylic acid group (-COOH)
attached to the main alkyl chain.

Their names end with -oic acid.

As substituent = carboxyl-.
IUPAC name: Methanoic acid

Common name: Formic acid

Commercially important carboxylic acids
Acetic acid Benzoic acid Lactic acid

Ethanoic acid Benzoic acid 2-hydroxypropanoic

acid
Commercially important carboxylic acid
Salicylic acid

2-hydroxybenzoic acid

antimicrobial
Precursor of aspirin
 Name this carboxylic acid
methyl
9 7 3
6 5
2 1
8 4

ethyl

2-ethyl -5-methyl nonanoic acid

E. Esters
Esters (symbolized as RCOOR’) are derived from the
carboxylic acid group where the -OH group is replaced
with the O-alkyl (alkoxyl) group. Esters are derived
when a carboxylic acid and alcohol reacts with one
another, leaving H2O as the other product.
Their names end with -oate.
As substituent alkoxycarbonyl-.
 Name this ester

main substituent
 Name this ester

1 3 5
1
2 2 4
pentyl
ethanoate

pentyl ethanoate
 Name this ester

pentyl methyl
4 2 2
5 3 1 1 3

hydroxy propanoate

3-hydroxy -2-methyl pentyl propanoate

C4H8O2 have 2 possible isomers

Butanoic acid methyl propanoate

Functional isomers
Functional Isomerism
isomerism in which 2 compounds have the
same number of atoms but they differ in
the arrangement of atoms which are
determined as different functional groups
in the compounds.
F. Ethers
These (symbolized as ROR’) composed or alkoxy
group (RO-) attached to the main alkyl chain.
Its name starts with alkoxy- and ends with parent
alkyl chain name.
In naming ethers, make the shorter alkyl chain as the
substituent and make the longer alkyl chain as the
parent chain.
As substituent alkoxy-.
 Name this ether
2
1

ethoxy 1

2
ethane

ethoxyethane
 There are 2 identical (same
length) ethyl groups (CH3CH2-)
attached to central oxygen

There is 1 methyl (CH3-) group

(shorter) and 1 propyl
(CH3CH2CH2-) group (longer)
attached to central oxygen

C4H10O
Metamers
Metamerism

isomerism in which the isomers have

different carbon chain length along a
functional group with hetero atom.
IV. Groups Containing Nitrogen
1. Amine
a. Primary amine
Symbolized as RNH2, primary Amine has only 1 alkyl
group and the two (2) hydrogen atoms are attached to
nitrogen.
Its name ends with -amine.
As a substituent = amino-.
 Name this amine
1

4 2
5 3 H

2-pentanamine
 b. Secondary amine
Written generally as R2NH, it has 2 alkyl groups and
the 1 hydrogen atom is attached to nitrogen.

Its name is N-alkyl-N-alkylamine.

 Name this amine
1

4 2
5 3 methyl

N-methyl -2-pentanamine
c. Tertiary amine
It is symbolized as R3N where 3 alkyl groups are
attached to a nitrogen.

Its name N-alkyl-N-alkyl-N-alkylamine.

Name the alkyl substituent in alphabetical
order.
IV. Groups Containing Nitrogen
1. Amide
This (symbolized as RCONH2) is a carboxylic acid
group derivative where OH is replaced by NH2 group.
Its name is alkylamide.

Its name ends with -amide.

As a substituent = amido-.
 Name this amide

4 3 2 1

butanamide
Table of Functional Group Nomenclature Priorities