Organic Chemistry

(Dana P.) #1
Section 1.7 Bonding in Methane and Ethane: Single Bonds 27

s orbital

the s orbital adds to
the lobe of the p orbital

p orbital the s orbital subtracts from
the lobe of the p orbital

>Figure 1.10
The sorbital adds to one lobe of
the porbital and subtracts from the
other lobe of the porbital.

p

s

pp
sp^3 sp^3 sp^3 sp^3

hybridization

H

H

a. b.

H

H

C C

>Figure 1.12
(a) The four orbitals are
directed toward the corners of a
tetrahedron, causing each bond
angle to be 109.5°.
(b) An orbital picture of methane,
showing the overlap of each
orbital of carbon with the s
orbital of a hydrogen. (For clarity,
the smaller lobes of the
orbitals are not shown.)

sp^3

sp^3

sp^3

with one sorbital to form the hybrid orbitals.) Each orbital has 25% scharacter
and 75% pcharacter. The four orbitals are degenerate—they have the same energy.


Like a porbital, an orbital has two lobes. The lobes differ in size, however, be-
cause the sorbital adds to one lobe of the porbital and subtracts from the other lobe of
the porbital (Figure 1.10). The stability of an orbital reflects its composition; it is
more stable than a porbital, but not as stable as an sorbital (Figure 1.11). The larger
lobe of the sp^3 orbital is used in covalent bond formation.


sp^3

sp^3

pp p
s

sp^3 sp^3 sp^3 sp^3

hybridization

4 orbitals are hybridized

hybrid orbitals

sp^3

sp^3

>Figure 1.11
An sorbital and three porbitals
hybridize to form four orbitals.
An orbital is more
stable than a porbital, but not as
stable as an sorbital.

sp^3

sp^3

The four orbitals arrange themselves in space in a way that allows them to get
as far away from each other as possible (Figure 1.12a). This occurs because electrons
repel each other and getting as far from each other as possible minimizes the repulsion
(Section 1.6). When four orbitals spread themselves into space as far from each other
as possible, they point toward the corners of a regular tetrahedron (a pyramid with four


sp^3
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