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J. Gillespie - 1950s
Stereochemistry
Count # of regions of high electron density on central atom VSEPR tells the geometry around central atom
electronegativity
differences
VSEPR Theory
regions of high electron density around the central atom go as far apart as possible to minimize repulsions five basic shapes
based
VSEPR Theory
Two regions of high electron density
VSEPR Theory
Three regions of high electron density
VSEPR Theory
Four regions of high electron density
VSEPR Theory
Five regions of high electron density
VSEPR Theory
Six regions of high electron density
VSEPR Theory
by the locations of regions of high electron density around the central atom(s)
molecular geometry
determined
VSEPR Theory
CH4 - methane electronic geometry
bond angles = 109.5o
tetrahedral
molecular geometry
tetrahedral
VSEPR Theory
H2O - water electronic geometry
tetrahedral
molecular geometry
bent or angular
VSEPR Theory
lone pairs of electrons (unshared pairs) require more volume than shared pairs there is an ordering of repulsions of electrons around central atom
VSEPR Theory
1
2
3
lone pair to lone pair repulsion is strongest lone pair to bonding pair repulsion is intermediate bonding pair to bonding pair repulsion is weakest mnemonic for repulsion strengths
lp/lp > lp/bp > bp/bp
lone pair to lone pair repulsion is why bond angles in water are less than 109.50
Hybrid Orbitals
Electronic Structures Formulas 1s 2s 2p Be 3s 3p Cl [Ne]
Lewis
Be . Cl
Hybrid Orbitals
Dot Formula
Cl Be Cl
Electronic Geometry
Cl Be Cl 180o - linear
Hybrid Orbitals
VSEPR
Polarity
Cl - Be - Cl Electroneg ativities 3.5 1.5 3.5
2.0 2.0
Cl Be Cl
180o-linear
Hybrid Orbitals
VSEPR
Polarity
Cl - - - Be - - - Cl
Cl Be Cl
180o-linear
Hybrid Orbitals
Molecular Geometry
Hybrid Orbitals
Valence Bond Theory (Hybridization) 1s 2s 2p 1s sp hyb 2p Be 3s 3p Cl [Ne]
Hybrid Orbitals
examples
BF3, BCl3
Hybrid Orbitals
Electronic Structures Formulas 1s 2s 2p B 3s 3p Cl [Ne]
Lewis
B.
. Cl
Hybrid Orbitals
Dot Formula
Cl B Cl Cl
Electronic Geometry
120-trigonal planar
Hybrid Orbitals
VSEPR
Cl Cl
Polarity
B - Cl Electroneg ativities 1.5 3.0
1.5
Cl 120-trigonal planar
Hybrid Orbitals
Molecular Geometry
Hybrid Orbitals
Hybrid Orbitals
examples
CH4, CF4, CCl4, SiH4, SiF4
Hybrid Orbitals
Electronic Structures
Lewis Formulas
C [He]
2s
2p
.. .C .
Hybrid Orbitals
Electronic Structures
Lewis Formulas
C [He] H
2s 1s
2p
.. .C . H.
Hybrid Orbitals
Dot Formula
Electronic Geometry
..
H .. . . .H H.C .. H
. .
C ..
. .
Hybrid Orbitals
VSEPR H
H C H H
Polarity
C - H Electroneg ativities 2.5 2.1
0.4
tetrahedral
Hybrid Orbitals
Molecular Geometry
Hybrid Orbitals
Valence Bond 2s 2p four sp3 hybrid orbitals C [He] C [He] 1s H
Hybrid Orbitals
Examples
PF5, AsF5, PCl5, etc.
Hybrid Orbitals
Electronic Structures
Lewis Formulas
4s
4p
2p
. As . . F .
Hybrid Orbitals
Dot Formula
F F As F
Electronic Geometry
As trigonal bipyramidal
F F
Hybrid Orbitals
VSEPR
F F F As F F
Polarity
As - F Electroneg ativities 2.1 4.0
1.9
trigonal bipyramid
Hybrid Orbitals
VSEPR
F F F As F F
Polarity
F F F As F F
symmetric dipoles cancel nonpolar molecule
trigonal bipyramid
Hybrid Orbitals
Molecular Geometry
Hybrid Orbitals
As [Ar] 3d10
Valence Bond
(Hybridization)
Hybrid Orbitals
Example
SF6, SeF6, SCl6, etc.
Hybrid Orbitals
Electronic Structures
Lewis Formulas
. Se . F.
Hybrid Orbitals
Dot Formula
F F F Se F F F
Electronic Geometry
Se octahedral
Hybrid Orbitals
VSEPR
F F F F Se F F octahedral
Polarity
Se - F Electroneg ativities 2.4 4.0
1.6
Hybrid Orbitals
VSEPR
F F F F Se F F octahedral
Polarity
F F F F Se F F
symmetric dipoles cancel nonpolar molecule
Hybrid Orbitals
Molecular Geometry
H H C C H H
H or H C C
H H
VSEPR
suggests C atoms at center of two equilateral triangles
H
C C
2s C
2p
C atoms are sp2 hybridized with single electrons in each of the lobes Top view
The unhybridized 2p orbital on the C atom lies perpendicular to the planar sp2 lobes. Side view
C=C double bond results from head-on overlap of two sp2 hybrid orbitals
The portion of the double bond formed from the head-on overlap of the sp2 hybrids is designated as a s bond.
The other portion of the double bond, resulting from the side-on overlap of the p orbitals, is designated as a p bond.
H C C H
or
H C C H
VSEPR
suggests C and H atoms are 180o apart.
2s
2p
two sp hybrids
2p
C C
Synthesis Question 1
The basic shapes that we have discussed are present in essentially all molecules. Shown below is the chemical structure of vitamin B6 phosphate. What is the shape and hybridization of each of the indicated atoms in vitamin B6 phosphate?
5 4 OH N H
+
H O O O P O 2 1 3 H2 C
CH 3
Synthesis Question 1
trigonal planar sp2 5 4 bent or angular sp3 OH N trigonal planar sp2 1 H 3 trigonal planar sp2 2 tetrahedral sp3
+
H O O O P O H2 C
CH3
Group Question 1
Shown below is the structure of penicillin-G. What is the shape and hybridization of each of the indicated atoms in penicillin-G?
5 3 2 CH 3 S H NH H O C CH C H CH 3 C N CH C C C CH 2 OH C O H O C C H H 9 8 10 4 6
Synthesis Question 2
As we all know, in the wintertime we are more likely to get shocked when we walk across carpet and touch the door knob. Here is another wintertime experiment to perform. Turn on a water faucet until you have a continuous but small stream of water coming from the faucet. Brush your hair vigorously then hold the brush near the stream of water. You will notice that the stream bends towards the brush. Why does the water bend?
Synthesis Question 2
Since water is a highly polar molecule, it is attracted by the electromagnetic field generated by the hair brush. This causes the stream to bend.
Group Question 2
On a recent infomercial it was claimed that placing a small horseshoe magnet over the fuel intake line to your cars carburetor would increase fuel mileage by 50%. The reason given for the mileage increase was that the magnet aligned the molecules causing them to burn more efficiently. Will this work? Should you buy this product?