CHM 121

ORGANIC CHEMISTRY I
Learning Outcome
At the end of the section, the students should be able to:
 Explain the meaning of hybrid orbitals,
 Define hybridization,
 Explain bonding in, and structure of methane (hybridization),
 Explain and sp hybridization of carbon and
 Draw/write expanded, condensed and line structures of simple
organic compounds.
NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA
 HYBRID ORBITALS
H

H C H Methane is a simple organic compound consisting of one

H
carbon atom bonded to 4 hydrogen atoms
Methane

• All bond lengths and bond angles in methane are the same
3

• Recall valence electron configuration of carbon (2s22p2)

•
If methane formed 4 bonds using valence electrons, two bonds would
be expected to be different (2s and 2p orbitals are different). But the
4 bonds in methane are the same.
Surmise: The 4 orbitals responsible for the bonds in methane must be
•

the same 4

2
 HYBRID ORBITALS
HYBRIDIZATION

2p

s orbital
Carbon’s atomic orbitals mix to form hybrid
2s orbitals. The 2s orbital and all three 2p
p orbital orbitals in a valence shell combine to
3

1s
produce four (4) sp3 hybrid orbitals. The
orbital produced is neither pure s nor pure p,
•
but it is a hybrid.
• When carbon atoms form bonds with each other, we describe the
resulting bonds using hybrid orbitals, which are formed by mixing
(hybridizing) the carbon’s atomic orbitals. (Linus Pauling, 1950s)
•

• When carbon atoms bond to 4 other atoms, the 2s orbital and all three
4

2p orbitals in the valence shell combine to produce four sp3 hybrid

orbitals:
2
 HYBRID ORBITALS
HYBRIDIZATION

3
sp
2s 2p
1 atomic 3 atomic 4 hybrid orbitals 3

orbital orbitals

OR • All four (4) sp3 hybrid

2p
orbitals are at the same
Hybridization energy level, with one
2s
•
electron in each hybrid
1s 1s
orbital
4

Energy

2
 HYBRIDIZATION

› THE SHAPE OF AN sp3 Carbon

To minimize electron-electron repulsion, the orbitals move as far apart
as possible. The compromise is that sp3 orbitals are arranged in the
shape of a tetrahedron around the central carbon atom, with bond
angles of 109.5o. It is represented as thus:

0
109.5
3
sp
3
3
sp
sp

NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA

 sp2 HYBRIDIZATION of CARBON

Hybridization of the 2s with two 2p orbitals results in the

formation of three(3) sp2 hybrid orbitals of equivalent energy.
One(1) 2p orbital remains unhybridized

2p

Hybridization
sp
2 2p z
2s

1s 1s

Energy + + 120
0

2s 2px 2py
Trigonal

NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA

 sp2 HYBRIDIZATION of CARBON
2p + + 120
0

Hybridization
2 2pz
sp 2s 2px 2py
2s Trigonal

1s 1s

Energy

The three sp2 hybrid orbitals are in the same plane and try to be as
far apart from each other as possible. They are at 1200 to each
other.
The simplest double bond compound is ethene. The two
unhybridized (2px) orbital on the two carbon atoms overlap in a
parallel fashion to form p bond.

NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA

 3

•
Formation of p bond by overlap of unhybridized (2pz)
orbital. Overlap above and below plane of double
bond 4

2
 sp Hybridization of Carbon

› Two (2) sp hybrid orbitals are derived from the hybridization of 2s with
only one of the 2p orbitals, leaving two (2) 2p orbitals [2py, 2pz]
unaffected.

2p
The 2 unhybridized p orbitals on two
carbons overlap to form two(2) p
Hybridization
sp 2py 2pz
2s

1s 1s
bonds at 900 to each other and to the
Energy
plane of the C-C bond, as in Ethyne
(acetylene)

NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA

sp Hybridization: Bonding in ethyne

2
 SIGMA (s) AND PI (p) BONDS

› Covalent bonds are formed as a result of overlap of atomic orbitals. The

overlap of atomic orbitals gives rise to molecular orbitals.
› • Head-to-head overlap of orbitals results in sigma bond
› Examples:

overlap of 2 overlap of 2 overlap of s

s orbitals p orbitals and p orbital

› The bonding electrons in the sigma bond are located along an imaginary
line joining the nuclei of the atoms concerned.

NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA

 PI (p) BOND

› The lateral overlap of 2 p orbitals of adjacent carbon atoms results in the

formation of pi bond
H 2 H H
C sp H
sp
2
C C C
H H H
H

H H
H H
C C C C
H H
H H

› Note: Pi bond is a weak bond. Here, the bonding electrons are located away from
the imaginary line joining the nuclei of the atoms concerned. Pi bonds are weaker
than sigma bonds because of less overlap.

NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA

 CARBON ATOM BONDING
A special characteristic of carbon is that it can form stable
single, double and triple bonds with other atoms. These
bonding patterns are adequately described by the model that
uses overlap of atomic orbitals.
BONDING IN ETHANE
3

The simplest organic compound that contains a C-C bond is ethane

(C2H6).
Bonds arise from the overlap• of orbitals on adjacent atoms.
•End-to-end overlap of sp3 orbitals produces a sigma (s) bond.
• All single bonds are s bonds
• Free rotation is possible • around s bonds
Each carbon in ethane molecule, CH3CH3 is sp3- 4

hybridized and tetrahedral in shape. Free rotation is

possible around C-C bond. 2
 CARBON CHAINS
›Each carbon atom can form FOUR bonds either to other carbon
atoms, or to different atoms (such as H, O, N, S, P, F, etc.)
C C C C C C

C
C
C C C C C C C
Etc

C C C C Single bond results fromsharing of 2 electrons

C C C C Double bond results from the sharing of 4 electrons

C C C C Triple bond results from the sharing of 6 electrons

NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA

 DRAWING ORGANIC COMPOUNDS
1. Expanded Structural
Formulas: In Expanded 2. Condensed Structural Formula: In condensed
Structural Formulas all atoms structural formulas, only specific bonds are shown.
andHbonds This is useful in reducing the number of C-H bonds
H are shown
H H H
that must be drawn.
H C C H H C C C H
H3C CH3 CH3 CH3 CH3CH3
H H H
H H H3C CH2 OH CH3CH2OH
H H
H C C O H H C O C H H3C CH2 O CH2 CH3
H H H H CH3CH2OCH2CH3

NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA

 DRAWING ORGANIC COMPOUNDS
3. LINE DRAWINGS: In line drawings (line-angle formulas, skeletal
structures, stick figures), bonds are represented by lines; everywhere two
lines meet or a line begins or ends is a carbon atom. H’s on C’s are not
shown except for emphasis. H’s on other atoms must be shown.

OH O
CH3
CH3
H H H H
H C C C C H H3C CH2 CH2 CH3
CH3(CH2)2CH3 CH
H H H H
Expanded structural formula Condensed structural formula Line drawing
C
CH2

NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA

 WORKED EXAMPLES
› 1. Draw the: i. Expanded (Lewis) structure and ii. Line structure of the
compounds: a. CH3CH2CH2CH(CH3)CH2CH3 b. CH3CHCHCH(CH3)CH2CH3
› 2. Convert the following condensed structures into line structures
› i. CH3(CH2)3CH3 ii. (CH3)3CCH2CH3
› 3. Convert the following line structures to condensed structures

ASSIGNMENT
1. Draw the line structure of: CH3(CH2)7CH=CH(CH2)8CH3
CH3
2. Draw the line structure of CH3
CH3 C CH
CH3
CH3

NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA

NASARAWA STATE UNIVERSITY, KEFFI, NIGERIA