Homework-lec #2.

Should the shape of an sp3 orbital look

more like an s or more like p orbital?
WHY?

more like p orbital. sp3 has 25% s

character, 75% p character

HYBRIDIZATION

1.9 Hybridized Atomic

Given the electron
configuration for C
Orbitals
and H, imagine how their atomic
orbitals might overlap

Would such orbital overlap

yield methane?
Copyright 2015 John Wiley & Sons, Inc. All rights reserved.

1-3

Klein, Organic Chemistry 2e

1.9 Hybridized Atomic

To make methane,
the C atom must
Orbitals

have 4 atomic orbitals available for

overlapping
If an electron is excited from the 2s to
the 2p, will that make it suitable for
making methane?

If four H atoms were to come in and

Copyright 2015 John Wiley & Sons, Inc. All rights reserved.

1-4

Klein, Organic Chemistry 2e

1.9 Hybridized Atomic

The carbon must
undergo hybridization
Orbitals

to form 4 equal atomic orbitals

The atomic orbitals must be equal in
energy to form four equal-energy
symmetrical C-H bonds

Copyright 2015 John Wiley & Sons, Inc. All rights reserved.

1-5

Klein, Organic Chemistry 2e

1.9 Hybridized Atomic

To make CH4, Orbitals
the 1s atomic orbitals of

four H atoms will overlap with the four

sp3 hybrid atomic orbitals of C

Copyright 2015 John Wiley & Sons, Inc. All rights reserved.

1-6

Klein, Organic Chemistry 2e

Draw a picture that shows the

necessary atomic orbitals and
their overlap to form ethane
(C2H6).

thene (ethylene).

Each carbon in ethene must bond to

three other atoms, so only three
hybridized atomic orbitals are
needed.
How do we describe the
hybridization process??

Hybridization in Ethene

An sp2 hybridized carbon

have :
three equal-energy sp2
orbitals

Bonding in Ethene

The sp2 atomic orbitals overlap

to form sigma () bonds
The unhybridized p orbitals in
ethene form pi () bonds, SIDEBY-SIDE overlap

nsider the structure of formaldehyde:

sp2
atomic
pi bond
orbital
sp2
atomic
orbital

Ethyne (acetylene).

Each carbon in ethyne must bond to two

other atoms, so only two hybridized atomic
orbitals are needed
How do we describe the
hybridization process??

Hybridization in Ethene

The sp atomic orbitals overlap

HEAD-ON to form sigma ()
bonds while the unhybridized p
orbitals overlap SIDE-BY-SIDE to

Which should be stronger, a pi bond

or a sigma bond? WHY?

Which should be longer, an sp3 sp3 sigma

bond overlap or an sp sp sigma bond
overlap?

Molecular Geomet

Molecular Geometry
Valence shell electron pair repulsion (VSEPR
theory)
Valence electrons (bonded and lone pairs)
repel each other
To determine molecular geometry
1.Determine the Steric number

 Valence shell electron pair repulsion

(VSEPR theory)
Valence electrons (bonded and lone pairs)
repel each other

To determine molecular geometry

2.Predict the hybridization of the central
atom

If the Steric number is 4, then it is sp3

If the Steric number is 3, then it is sp2
If the Steric number is 2, then it is sp

Geometry
For any sp3 hybridized atom, the 4 valence
electron pairs will form a tetrahedral
Methanegroup geometry
The bond
How does
electron
has 4 equal
bonds, so
the bond
angles are
equal

the lone
pair of
ammonia
affect its
geometry?

Copyright 2015 John Wiley & Sons, Inc. All rights reserved. 1-20

angels in
oxygen are
even
smaller,
why?

Klein, Organic Chemistry 2e

sp3 Geometry
The molecular geometry is different
from the electron group geometry.
HOW?

Copyright 2015 John Wiley & Sons, Inc. All rights reserved. 1-21

Klein, Organic Chemistry 2e

 Calculate the Steric number for BF3

Electron pairs that are located in sp2
hybridized orbitals will form a trigonal
planar electron group geometry
What will be the molecular geometry?

Analyze the steric number, hybridization,

electron group geometry and
molecular geometry for this imine?

Analyze
the
Steric
number,
the
hybridization,
the
electron
group
geometry, and the molecular geometry
for the following molecules

CO2