ORGANIC CHEMISTRY D. F. Palacio, RPT.

Carbon, in combination with hydrogen,

oxygen, nitrogen, and sulfur, forms the
basis for millions of organic compounds.

Organic molecules form the products used

in:
1. Cosmetics and perfumes
2. Pharmaceutical products
3. Soaps and detergents
4. Paints, varnishes, dyes
5. Many more!

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THE CARBON
ATOM: BONDING
AND SHAPE

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 The carbon atom is central to all organic
compounds.

A carbon atom usually forms four covalent

bonds.
Single bonds
Ex: H3C-CH3 in ethane
Double bonds
Ex: H2C=CH2 in ethene
Triple bonds
Ex: HCCH in ethyne (acetylene)

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An organic compound is classified as saturated if it contains
only single bonds.
Ex: H3C-CH3 in ethane

An organic compound is classified as unsaturated if the

molecules possess one or more multiple carbon-carbon
bonds.
Ex: H2C=CH2 in ethene
Ex: HCCH in ethyne (acetylene)

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THE SHAPES OF CARBON-
CONTAINING COMPOUNDS
Valence Shell Electron Pair Repulsion theory (VSEPR)

VSEPR theory states that electron pairs repel each

other because they have like charges.

The electron pairs will try to spread out as far as

possible around an atom.

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Figure 19.1 Tetrahedral structure of carbon: (a) a regular
tetrahedron; (b) a carbon atom with tetrahedral bonds;
(c) a carbon atom within a regular tetrahedron; (d) a
methane molecule, CH4

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Figure 19.2 (a) Lewis structure for C2H4. (b) Shape of a molecule with
a carbon-carbon double bond. The hydrogens and carbon form the
vertices of a triangle. The bond angles are 120.

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In a triple bond, the carbon has only two regions
for shared electrons. To be placed as far apart as
possible, a linear arrangement is required.
180

H:C:::C:H H C C H

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MOLECULAR MODELS
Models are often used in organic chemistry to illustrate
molecules.

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Figure 19.3 Molecular models of methane:
(a) ball-and-stick model; (b) spacefilling
model
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FIGURE 19.4 MODELS OF ETHANE: (A)
LEWIS STRUCTURE; (B) BOND-LINE
DRAWING; (C) BALL-AND-STICK MODEL;
(D) SPACEFILLING MODEL

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STRUCTURAL FORMULAS
In a structural formula, the arrangement of atoms within
the molecule is clearly shown.
These structural formulas are often shortened into
condensed structural formulas.
e.g. CH3CH2CH3 & CH3-CH2-CH3

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CLASSES OF
ORGANIC
COMPOUNDS

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CLASSIFYING
ORGANIC
COMPOUNDS

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FUNCTIONAL GROUPS
Organic compounds with similar structures are grouped
into classes as shown in Table 19.1.

The members of each class of compounds contain a

characteristic atom or group of atoms called a
functional group.

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FUNCTIONAL GROUPS
A functional group:
is part of a larger molecule.
is composed of an atom or group of atoms that have
characteristic chemical behavior.
Chemically, a given functional group behaves in nearly
the same way in every molecule its part of.

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 ISOMERISM
The phenomenon of two or more compounds having the same
molecular formula but different structural arrangements of their
atoms is called isomerism.
The various individual compounds are called isomers.
e.g. There are two isomers of C4H10.

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Figure 19.8 Ball-and-stick models illustrating
structural formulas of butane and isobutane.

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ISOMERS

Isomers are compounds that have the

same molecular formula, but different
structural formulas.

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EXAMPLE FOR
DRAWING ISOMERS

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 There are three isomers of pentane, C4H12. Write
structural formulas and condensed structural
formulas for these isomers.
1. Write the carbon skeleton of the compound containing the
longest continuous carbon chain.
C-C-C-C-C
2. Complete the structure by attaching hydrogen atoms
around each carbon.
H H H H H

H C C C C C H CH3CH2CH2CH2CH3

H H H H H
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 Isomers of Pentane, C5H12 (continued)
Forthe next isomer, start by writing a four-carbon chain
and attach the fifth carbon atom to either of the middle
carbon atoms do not use the end ones. Add 12
hydrogens to complete the structure.
H
H H
H H C H
CH3

H C C C C H CH3CH2CHCH3 CH3CH2CH(CH3)2

H H H H

This is the only four-chain compound that can be

written.

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 Isomers of Pentane, C5H12 (continued)
For the third isomer, start with a three-
carbon chain, attach the other carbon atoms
to the central carbon atom, and complete the
structure by adding 12 hydrogen atoms:
H
H H
H C H CH3 No more isomers of
C5H12 can be written.
H C C C H CH3CCH3
H C H
CH3
H H
H

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INTRODUCTION TO
THE
REACTIONS OF
CARBON
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 One of the most
important carbon
reactions is oxidation
reduction.
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 Oxidation

When carbon atoms are oxidized, they often

form additional bonds to oxygen.
H

H C H + 2 O2 O C O + 2H2O

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 Reduction

When carbon atoms are reduced,

they often form additional bonds to
hydrogen.
H

O C O + 3 H2 H C OH + H2O

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Other Reactions of Carbon

1. Substitution reactions

2. Elimination reactions

3.Addition reactions

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 Substitution Reaction
If, in a reaction, one atom in a molecule
is exchanged by another atom or group of
atoms, a substitution reaction has taken
place.
H H

H C H + Br2 H C Br + HBr

H H
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 Elimination Reaction
An elimination reaction is a reaction in
which a single reactant is split into two
products, and one of the products is
eliminated.
Elimination reactions form multiple bonds.
H H H H

H C C Br C C + HBr

H H H H
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 Addition Reaction
Two reactants adding together to form a
single product is called an addition
reaction.
An addition reaction can be thought of as
the reverse of an elimination.
H H H H

C C + HBr H C C Br

H H H H 38
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