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Hybridized Orbitals. V-B theory can’t explain some observations about molecular compounds without the concept of hybridized orbitals. i.e., covalent (NM/NM) compounds. …the result then being…. …the central atom SHOULD be…. …but is ACTUALLY hybridized to be…. (LS). In….

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slide1

Hybridized Orbitals

V-B theory can’t explain some observations about

molecular compounds without the concept of

hybridized orbitals.

i.e., covalent (NM/NM) compounds

slide2

…the result

then being…

…the central atom

SHOULD be…

…but is ACTUALLY

hybridized to be…

(LS)

In…

2 hyb. sp orbs.

2 unhyb. 2p orbs.

BeF2

2s

2p

sp

2p

3 hyb. sp2 orbs.

1 unhyb. 2p orb.

BF3

2s

2p

2p

sp2

CH4

4 hyb. sp3 orbs.

2s

2p

sp3

:

:

:

F

:

:

:

:

:

F

Xe

F

:

:

H2O

:

4 hyb. sp3 orbs.

:

:

:

:

:

F

:

:

:

P

F

F

F

:

2s

2p

sp3

:

:

:

H

:

:

:

5 hyb. sp3d orbs.

4 unhyb. 3d orbs.

:

:

:

F

F

B

F

PF5

H

C

H

:

:

:

:

:

:

:

:

:

F

Xe

F

:

:

H

:

3s

3p

3d

3d

:

:

sp3d

:

:

:

F

F

:

H

O

:

:

:

:

H

:

:

F

Be

F

:

:

5 hyb. sp3d orbs.

4 unhyb. 5d orbs.

XeF2

5s

5p

5d

5d

sp3d

6 hyb. sp3d2 orbs.

3 unhyb. 5d orbs.

XeF4

5s

5p

5d

5d

sp3d2

slide3

KEY: EDG  hybridization of central atom

linear  sp

trig. planar  sp2

tetrahedral  sp3

trig. bipyr.  sp3d

octahedral  sp3d2

slide4

sp hybridization

sp hybridization occurs when one s and one of the three p

orbitals hybridize. It results in the creation of two sp hybrid

orbitals (orange). The other two p orbitals (purple) are

unhybridized; they retain the “figure-8” or “dumbbell” shape.

slide5

The bonds

in ammonia

are s bonds.

..

N

H

H

H

Multiple Bonds

s (sigma) bonds are bonds in which the e– density is

along the internuclear axis.

-- These are the single bonds we have

considered up to this point.

-- e.g., s-s, s-p, or p-p overlap,

and also p-sp hybrid overlap

sigma (s) = single

Multiple bonds result from the overlap of two p orbitals

(one from each atom) that are oriented perpendicularly

to the internuclear axis. These are p (pi) bonds.

pi, multiple, unhybridized

slide6

H

H

C=C

H

H

H

H

C

C

H

H

p bonds are generally weaker than s bonds because

p bonds have less overlap.

For ethene (C2H4)…

For each carbon atom, there

are 3 sp2 hybridized

orbitals; these form s

bonds (- - - -) with C or H.

Where unhybridized

orbitals overlap,

a p bond ( ) is formed.

slide7

Single bonds

are s bonds.

e.g., C2H6

Double bonds consist of

one s and one p.

e.g., C2H4

Triple bonds consist of

one s and two p.

e.g., C2H2

slide8

Experiments indicate that all

of C2H4’s atoms lie in the

same plane. This suggests

that p bonds introduce

rigidity (i.e., a reluctance

to rotate) into molecules.

-- p bonding does NOT occur with sp3 hybridization,

only sp and sp2

-- p bonding is more prevalent with small molecules

(e.g., C, N, O)

(Big atoms don’t allow enough

p-orb. overlap for p bonds to form.)

slide9

[ ]

..

..

O

..

..

O–

N

=O

..

..

..

..

Delocalized p Bonding

Localized p bonds are between…

two atoms only.

-- e.g.,

C2H2, C2H4, N2

Delocalized p bonds are

“smeared out” and

shared among…

> two atoms.

-- These are common for

molecules with…

resonance structures.

The nitrate ion (NO3–) has

delocalized electrons.

-- The electrons involved in

these bonds are delocalized electrons.

slide10

H

H

a 2p

orbital on each C

that is oriented

to plane of m’cule.

C

C

C

C

H

H

C

C

H

H

Consider benzene, C6H6.

-- Each carbon atom is

___ hybridized.

sp2

-- This leaves...

-- 6 e– shared equally by 6 C atoms

slide11

O

=

..

..

H

H

O

H3C–C–CH3

=

H–C–C–C–H

H

H

O

..

..

..

..

..

O–S=O

..

..

[ ]

O

..

..

2–

..

..

..

..

O–

–O

..

S

..

..

..

..

Which of the following exhibit delocalized bonding?

24 e–

“NOPE.”

propanone

SO2

18 e–

“YEP.”

sulfur dioxide

(res.)

SO42–

32 e–

“NOPE.”

sulfate ion