Hybridization in Carbon

GENERAL CHEMISTRY 1
CHM 111 LECTURE 1
HYBRIDIZATION
Bonding in Carbon and
Orbital Hybridization
Structure
Structureof
ofMethane
Methane
tetrahedral
bond angles = 109.5°
bond distances = 110 pm
but structure seems inconsistent with
electron configuration of carbon
Electron
Electronconfiguration
configurationof
ofcarbon
carbon
only two unpaired

2p
electrons
should form 
bonds to only two
hydrogen atoms
bonds should be
2s at right angles to
one another
sp
sp3Orbital
3
OrbitalHybridization
Hybridization
2p
Promote an electron from the 2s

to the 2p orbital
2s
sp
sp3Orbital
3
Hybridization
2p 2p
2s 2s
sp
sp3Orbital
3
Hybridization
2p
Mix together (hybridize) the 2s

orbital and the three 2p orbitals
2s
sp
sp3Orbital
3
Hybridization
2p
2 sp3
4 equivalent half-filled
orbitals are consistent
with four bonds and
tetrahedral geometry 2s
Shapes
Shapesof
oforbitals
orbitals
s
Nodal
Nodalproperties
propertiesof
oforbitals
orbitals
p + –
s +
Shape
Shape of sp3hybrid
of sp 3
hybridorbitals
orbitals
p + –
take the s orbital and place it on

top of the p orbital
s +
Shape
Shape of sp3hybrid
of sp 3
hybridorbitals
orbitals
s+p + + –
reinforcement of electron wave in

regions where sign is the same
destructive interference in regions of
opposite sign
Shape
Shape of sp3hybrid
of sp 3
hybridorbitals
orbitals
sp hybrid + –
orbital shown is sp hybrid

analogous procedure using one s orbital
and three p orbitals gives sp3 hybrid
shape of sp3 hybrid is similar
Shape
Shape of sp3hybrid
of sp 3
hybridorbitals
orbitals
sp hybrid + –
hybrid orbital is not symmetrical

higher probability of finding an electron on
one side of the nucleus than the other
leads to stronger bonds
The C—HBond
TheC—H BondininMethane
Methane
In-phase overlap of a half-filled 1 s orbital of

hydrogen with a half-filled sp3 hybrid orbital of
carbon:
+
s H + C– sp3
gives a  bond.
+
H—C  H C–
Justification
Justificationfor
forOrbital
Hybridization
consistent with structure of methane

allows for formation of 4 bonds rather than 2
bonds involving sp3 hybrid orbitals are stronger
than those involving s-s overlap or p-p overlap
sp3 Hybridization
and Bonding in Ethane
Structure
Structureof
ofEthane
Ethane
C2H6
CH3CH3
tetrahedral geometry at each carbon

C—H bond distance = 110 pm
C—C bond distance = 153 pm
The C—CBond
TheC—C BondininEthane
Ethane
σ bonds are covalent bonds formed between atoms

when end-on overlap of orbitals occurs.
In-phase overlap of half-filled sp3 hybrid

orbital of one carbon with half-filled sp3
hybrid orbital of another.
Overlap is along internuclear axis to give a  bond.
The C—CBond
TheC—C BondininEthane
Ethane
In-phase overlap of half-filled sp3 hybrid

orbital of one carbon with half-filled sp3
hybrid orbital of another.
Overlap is along internuclear axis to give a  bond.
sp + sp + sp + sp
3 3 3 3
Because we combined the s orbital and all three p orbitals, we call these
new orbitals “sp3 orbitals”. There are four of them, each pointing
towards a corner of a tetrahedron, exactly where we want them.
Copyright © 2003 Charles B. Abrams
=Csp + Hs 3
Each of the C-H bonds in ethane, CH3CH3, can be described as the

combination of a carbon sp3 and a hydrogen 1s orbital. These are
cylindrically symmetrical, and are called sigma bonds ()
C sp + C sp
1 3 2 3
The bond between the two carbon atoms can be described as the
combination of an sp3 orbital on one carbon with an sp3 orbital on
the other carbon.
=C sp + C sp 1 3 2 3
The resulting combination is cylindrically symmetrical, and is therefore

called a sigma () bond. Because it is cylindrically symmetrical, this bond
can rotate without changing the overlap between the two sp3 orbitals
The next few slides show that rotating around the C-C bond in ethane
does not change the overlap of the two C sp3 orbitals, and therefore does
not change the bond in any way.
(Rotated 30 degrees)



(Rotated 120 degrees). This completes the discussion of bonding in
ethane.
sp2 Hybridization
and Bonding in Ethylene
Structure
Structureof
ofEthylene
Ethylene
C2H4
H2C=CH2
planar
bond angles: close to 120°
bond distances: C—H = 110 pm
C=C = 134 pm
sp
sp2Orbital
2
Hybridization
2p

to the 2p orbital
2s
sp
sp2Orbital
2
Hybridization
2p 2p
2s 2s
sp
sp2Orbital
2
Hybridization
2p

orbital and two of the three 2p
orbitals
2s
sp
sp2Orbital
2
Hybridization
2p
2 sp2
sp2 hybrid orbitals plus
1 p orbital left
unhybridized 2s
sp
sp2Orbital
2
Hybridization
p
2 of the 3 sp2 orbitals
2 sp2 are involved in  bonds
to hydrogens; the other
is involved in a  bond
to carbon
sp
sp2Orbital
2
Hybridization
p 

2 sp2
 

Bonding
BondingininEthylene
Ethylene
the unhybridized p orbital of

p carbon is involved in  bonding
to the other carbon
2 sp2
Bonding
BondingininEthylene
Ethylene
2 sp2
each carbon has an unhybridized 2p orbital

axis of orbital is perpendicular to the plane of the  bonds
Bonding
BondingininEthylene
Ethylene
A π bond is a covalent bond formed by the
sideways overlap of two parallel atomic orbitals.
2 sp2
side-by-side overlap of half-filled

p orbitals gives a bond
double bond in ethylene has a
 component and a  component
sp + sp + sp + pz
2 2 2
These hybrid orbitals are called sp2 orbitals. The complete set of orbitals
available for bonding now includes three sp2 orbitals and the p orbital
which was not involved in the hybridization.
=Csp + Hs 2
Each of the C-H bonds ethene, CH2=CH2, can be described as the

combination of a carbon sp2 and a hydrogen 1s orbital. These are
cylindrically symmetrical sigma bonds ()
C sp + C sp
1 2 2 2
There are two bonds between the carbon atoms. One of these can
be described as the combination of an sp2 orbital on one carbon
with an sp2 orbital on the other carbon.
=C sp + C sp 1 2 2 2
The resulting combination is cylindrically symmetrical, and is therefore

called a sigma () bond. Before we can decide if this bond can rotate, we
must consider the other bond in ethene.
C pz + C pz
1 2
The second bond between the carbon atoms can be described as the
combination of the p orbital on one carbon with the p orbital on the other
carbon. These two p orbitals are parallel and therefore have good overlap.
=C pz + C pz 1 2
The resulting combination is not cylindrically symmetrical; instead it has

a plane of symmetry. It is called a pi () bond. The p orbitals can only
overlap if they are parallel. This bond can not rotate.
However, what if carbon 2 was rotated …. (step through the next three slides to
see the rotation)
(rotated 45 degrees)

C pz + C py
1 2
(Rotated 90 degrees.) The p orbital on carbon 2 now does not overlap with the
p orbital on carbon 1. Because the p orbital now points in a different direction,
it is labeled with a different Cartesian coordinate. No pi bond can form.
Let’s rotate the carbon atom back to where it was, so that the p orbitals can
overlap… (rotated 45 degrees)
(Rotated 0 degrees.) Again the p orbitals can overlap, and a pi bond can form.

 
The carbon-carbon double bond in ethene can be described as one sigma

and one pi bond. The pi bond prevents the double bond from rotating. All
of the atoms (H and C) are in one plane, so this is a planar molecule.
The plastics shown here were
manufactured with ethylene.
Source: Comstock - Mountainside, NJ

Copyright © Houghton Mifflin Company. All rights reserved.
sp Hybridization
and Bonding in Acetylene
Structure
Structureof
ofAcetylene
Acetylene
C2H2
HC CH
linear
bond angles: 180°
bond distances: C—H = 106 pm
CC = 120 pm
sp
spOrbital
Hybridization
2p

to the 2p orbital
2s
sp
spOrbital
Hybridization
2p 2p
2s 2s
sp
spOrbital
Hybridization
2p

orbital and one of the three 2p
orbitals
2s
sp
spOrbital
Hybridization
2p 2p
2 sp2
sp hybrid orbitals plus
2 p orbitals left 2s
unhybridized
sp
spOrbital
Hybridization
2p
1 of the 2 sp orbitals
2 sp2
to hydrogen; the other
to carbon
sp
spOrbital
Hybridization
2p 

2 sp2 
Bonding
BondingininAcetylene
Acetylene
the unhybridized p orbitals of

2p carbon are involved in separate
 bonds to the other carbon
2 sp2
Bonding
Acetylene
2p
2 sp2
one  bond involves one of the p orbitals on each carbon

there is a second  bond perpendicular to this one
Bonding
Acetylene
2p
2 sp2
Bonding
Acetylene
2p
2 sp2
sp + sp + py + pz
These hybrid orbitals are called sp orbitals. The complete set of orbitals
available for bonding now includes these two sp orbitals and the two p
orbital which were not involved in the hybridization.
C sp + C sp
1 2
One bond between the carbons is described as the combination of the

carbon 1 sp orbital plus the carbon 2 sp orbital.
= C sp + C sp 1 2
This is called a sigma bond, as in the previous examples.

C py + C py
1 2
There are now two sets of p orbitals which can be combined. The p y
orbitals on each carbon can combine to form one pi bond…
=C py + C py 1 2
This is one of the pi bonds in ethyne.

C pz + C pz
1 2
The other set of p orbitals can also combine to form a second pi bond.

=C pz + C pz 1 2
Here is another pi bond in ethyne.




The triple bond in ethyne (acetylene) is described as one sigma bond and
two pi bonds.
What is the hybridization in each carbon atom?
4
2 5
6
3
7
1
sp3 – 2, 5 sp2 – 1, 3, 4 sp – 6, 7
tetrahedral trigonal planar linear
Allene, H2C=C=CH2
What is the hybridization?
The  clouds of the two double bonds are oriented

perpendicular to each other. Hence the hydrogens
are turned 90o. The is due to the original orientation
of the p orbitals on the center carbon atom.
Spartan 02
= C py + C py 2 3
This model shows the two pi bonds in allene, and makes it clear that
allene is not planar; not all of the atoms of allene are in the same plane.
Instead, allene is twisted.
1.19
Which Theory of
Chemical Bonding is Best?
POLAR COVALENT BONDS AND
ELECTRONEGATIVITY
 Electrons in covalent bonds are not necessarily shared equally by
the two atoms that they connect.
 greater tendency to attract electrons toward itself than the other,
we say the electron distribution is polarized, and the bond is
referred to as a polar covalent bond.
 Hydrogen fluoride has a polar covalent bond. Because fluorine
attracts electrons more strongly than hydrogen
 the electrons in the H±F bond are pulled toward fluorine, giving it
a partial negative charge, and away from hydrogen giving it a
partial positive charge.
δ–
δ+ F
H
POLAR COVALENT BONDS AND
.
ELECTRONEGATIVITY
 The tendency of an atom to draw the electrons in a covalent bond
toward itself is referred to as its electronegativity.
 An electronegative element attracts electrons; an electropositive

one donates them. Electronegativity increases across a row in the
periodic table.
 The most electronegative of the second-row elements is fluorine;

the most electropositive is lithium.
 Electronegativity decreases in going down a column. Fluorine is

more electronegative than chlorine.
Dipole and dipole moment
Centers of positive and negative charge that are separated from each other
constitute a dipole. The dipole moment of a molecule is equal to the
charge µ (either the positive or the negative charge, since they must be
equal) multiplied by the distance between the centers of charge:
µ=e xd
Polar and Non-polar Compounds
Polar Compounds : H2O, HCl, CH3Cl Non-Polar Compounds: CH4, C2H6
Shared electrons unevenly Shared electrons evenly
Have partial positive end and partial Have no Charges

negative end
Electronegativity must be 0.4 and above Electronegativity must be 0 or less than
0.4
Have stronger intermolecuar forces .i.e Have weaker intermolecuar forces .i.e
higher melting and boiling points lower melting and boiling points
Soluble in polar solvents Soluble in non-polar solvents
THE END

Hybridization in Carbon

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Hybridization in Carbon

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GENERAL CHEMISTRY 1

CHM 111 LECTURE 1

only two unpaired

Promote an electron from the 2s

Mix together (hybridize) the 2s

take the s orbital and place it on

reinforcement of electron wave in

orbital shown is sp hybrid

hybrid orbital is not symmetrical

In-phase overlap of a half-filled 1 s orbital of

consistent with structure of methane

tetrahedral geometry at each carbon

σ bonds are covalent bonds formed between atoms

In-phase overlap of half-filled sp3 hybrid

In-phase overlap of half-filled sp3 hybrid

Each of the C-H bonds in ethane, CH3CH3, can be described as the

The resulting combination is cylindrically symmetrical, and is therefore

Copyright © 2003 Charles B. Abrams

Copyright © 2003 Charles B. Abrams

Copyright © 2003 Charles B. Abrams

Promote an electron from the 2s

Mix together (hybridize) the 2s

the unhybridized p orbital of

each carbon has an unhybridized 2p orbital

side-by-side overlap of half-filled

Each of the C-H bonds ethene, CH2=CH2, can be described as the

The resulting combination is cylindrically symmetrical, and is therefore

The resulting combination is not cylindrically symmetrical; instead it has

Copyright © 2003 Charles B. Abrams

Copyright © 2003 Charles B. Abrams

The carbon-carbon double bond in ethene can be described as one sigma

Source: Comstock - Mountainside, NJ

Promote an electron from the 2s

Mix together (hybridize) the 2s

the unhybridized p orbitals of

one  bond involves one of the p orbitals on each carbon

One bond between the carbons is described as the combination of the

This is called a sigma bond, as in the previous examples.

Copyright © 2003 Charles B. Abrams

This is one of the pi bonds in ethyne.

Copyright © 2003 Charles B. Abrams

Copyright © 2003 Charles B. Abrams

Here is another pi bond in ethyne.

Copyright © 2003 Charles B. Abrams

The  clouds of the two double bonds are oriented

 An electronegative element attracts electrons; an electropositive

 The most electronegative of the second-row elements is fluorine;

 Electronegativity decreases in going down a column. Fluorine is

Have partial positive end and partial Have no Charges

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