Hybridization

Hybridization
• Tendency to form bonds is strong among atoms due to the
stabilization imparted by bond formation.
• More bonds formed; more stabilization achieved.
• The intermixing of pure atomic orbitals (s,p,d,f) in order to
form a new set of orbitals whose properties are quite distinct
from the original.
 Hybridization
Some atoms form more bonds than that expected of them
from the number of unpaired electrons in their valence shell.

In Carbon, hybridization occurs to create stable

compounds.
 Three Hybrid Bond Orbitals

1. Tetrahedral hybridization (sp 3 )

2. Trigonal hybridization (sp 2 )
3. Digonal hybridization (sp)
 Tetrahedral hybridization (sp 3)

Carbon can form four bonds with Hydrogen. C in its ground

state has an electronic configuration of : 1s 2 2s 2 2px 1 2py 1 2pz 0 which
can account for only two bonds.
If one electron in 2s is excited to 2p (molecules are not in the
orbital of lowest energy): 1s 2 2s 1 2px 1 2py 1 2pz 1 it cannot account for
four equivalent bonds.
 Tetrahedral hybridization (sp 3)

To account for the C-H bonds, the 2s and 2p orbitals are

hybridized. Various mathematical combinations of the s and p orbitals
are taken and the hybrid orbitals with the greatest degree of
directional character are chosen.
1s 2 2s 1 2px 1 2py 1 2pz 1
hybridized

1s 2 (2sp 3 ) 1 (2sp 3 ) 1 (2sp 3 ) 1 (2sp 3 ) 1

 Tetrahedral hybridization (sp 3)
In hybridization, the name of
the hybrid orbitals reflects the
number of each orbital hybridized;
the number of the hybrid orbitals
formed equals the number of atomic
orbitals combined. Thus, the 4 sp 3
hybrids are obtained for C.
 Tetrahedral hybridization (sp 3)
These hybrids orient themselves as
far apart from each other as possible,
resulting to the tetrahedral arrangement
and bond angle in CH 4 of 105.9 ⁰ , sp 3
hybrid has 25% s character and 75% p
character. Thus the 4 C-H bonds in
methane (CH 4 ) result from the overlap of 2
sp 3 – 1s orbitals of C and H respectively.
 Trigonal hybridization (sp 2)
C is capable of forming other types of hybrid orbitals. In
ethylene (C 2 H 4 ) each C atom is surrounded by three atoms and the C
is bonded to the other C atom by a double bond. The entire C-H
bonds are equivalent while the C=C bond consists of two types:
1. σ (sigma) bond – results from the head – on overlap of
orbitals.
2. π (Pi) bond – results from the lateral overlap of
orbitals.
 Trigonal hybridization (sp 2)
To account for the bonding pattern in ethylene, a different type
of hybridization is required for C:
1s 2 2s 1 2px 1 2py 1 2pz 1
hybridized

(2sp 2 ) 1 (2sp 2 ) 1 (2sp 2 ) 1 2pz 1

 Trigonal hybridization (sp 2)
Three equivalent sp 2 hybrids are formed
leaving a 2p orbital occupied by an unpaired
electron. The sp 2 hybrids when oriented as far
away from each other as possible adapt a
trigonal planar structure while the 2p orbital
lies perpendicular to the plane defined by the
sp 2 hybrids.
 Trigonal hybridization (sp 2)
Two of the sp 2 hybrids are used to bond
with the s orbital of H (σ bond), while the
other is used to with the p orbital of the other
C atom (π bond), sp 2 hybrid has 1/3 s
character and 2/3 p character. It results a
planar configuration at the angle of 120 ⁰.
 Digonal hybridization (sp)
Carbon atoms can likewise form sp
hybrids from one s and one p orbital:
1s 2 2s 1 2px 1 2py 1 2pz 1
h yb r id ized

(2sp) 1 (2sp) 1 2py 1 2pz 1

This hybridization is true for the C atoms
in acetylene (C2H2). This hybrid will have 50%
s character and 50% p character and forms an
angle of 180 ⁰ and results in linear
configuration.
 Hybridization
Carbon utilizes sp 3 hybrid if attached to 4 atoms (forms single
bond); sp 2 if attached to 3 atoms (forms double bond); and sp to 2
atoms (forms triple bond).

sp

sp3 sp2
Bond
Properties
 Bond Properties

1. Bond order
2. Bond dissociation energy
3. Bond length
4. Bond angle
5. Bond polarity
 Bond Order
• The number of bonds shared by two atoms
• Generally related to valency multiplicity between atoms in molecules.
Total bond order includes pi and sigma bonds; and mobile bond
order considers only the pi bonds.

Total Bond Order Mobile Bond Order

-C–C- 1 0
-C=C- 2 1
-C≡C- 3 2
 Bond Dissociation Energy
the amount of energy released or absorbed when a bond is
formed; measure of bond strength.

• The greater the bond polarity, the greater is the bond energy or bond
strength.
• The higher the s character the greater the bond strength.
• Bond energy increases as the bond length decreases.
• The greater the number of pi bonds the greater the bond strength.
• The bond energy decreases when there is loss of overlap of hybrid
orbitals.
 Bond Length
the intermolecular distance between two atoms sharing a
bond.

When two atoms approach each other,

their interaction is influenced by:
1. Repulsion between 2 electron clouds (-)
(-)
2. Repulsion between 2 nuclei (+) (+)
3. Attraction between the nucleus of each
and the electrons of the other (+) (-)
 Bond Angle
the angle between any two bonds in a molecule

• Bond angle about an atom is largely influenced by its hybridization.

sp3 – 109.5⁰ sp2 – 120⁰ sp - 180⁰

• The greater the number of lone pairs in a compound the smaller the
bond angle.
• The more electronegative the adjacent atom the smaller is the bond
angle.
 Bond Polarity
- Separation of charge in a bond
- Results from the unequal distribution of electrons between 2 atoms
sharing a bond due to differences in their electronegativity

Relative electronegativities of atoms found in organic molecules

F O N, Cl Br C, S, I H, P
4.0 3.5 3.0 2.8 2.5 2.1
 Bond Polarity
• As the polarity increases, the bond length decreases (inversely
proportional). The more polar the electrons, the more ionic it comes, and
the more attraction it comes, and the shorter the distance or the bond
length.

Type of Single Bond Bond length

C–C 1.538
C–N 1.471
Increasing Polarity
C–O 1.430
C–F 1.380
 Bond Polarity
• The lesser the s character, the lesser the ability to attract electrons; the
greater the s character, the greater the ability to attract the electrons and
it shortened the bond length.
• The attraction between the nucleus and the electrons is greater, the
greater the s character of the bond orbitals. (sp < sp 2 < sp 3 )
• The greater the number of bonds, the shorter the bond length
Single bond – sigma bonds
Double bond – sigma bond and pi bonds
Triple bond – sigma bond and 2 pi bonds
 Bond Polarity
• The electronegative the adjacent atoms the shorter the bond length.
• Pi and sigma electron delocalization affects the bond length.

Pi and Sigma electron delocalization shortened the bond length

Bond Length
Vinyl chloride CH2=CH-Cl 1.347
Methyl chloride CH3-Cl 1.384
Vinyl fluoride CH2=CH-F 1.726
Methyl fluoride CH3-F 1.781
 Bond Polarity
• Sigma electron delocalization
happened when an sp 3 orbital
bonded to a hydrogen to the
neighboring p orbital or towards
the pi bond. The C-C will have a
double bond character, and such
will be shortened.
 Bond Polarity

• This is not possible to CF 3 because of the F which has a high

electronegativity values.
Uses of Organic Compounds in Our
Daily Life
• Preservatives
• Drugs, including antibiotics
• Plastics
• Flavorings in food, food coloring, and color
• Scents
• Fuel
• Pesticides
• Laptop, cellphone, calculator, and TV screens
• Vitamins
• Cosmetics
Reference:

Calingasan, A. G. & Evangelista, A. D. (2012). Lectures in Organic

Chemistry: Modular Approach. pp. 7-15. Lyceum of the Philippines
University