The document discusses pushing electrons through various chemical reactions and processes involving electron deficient atoms or molecules. These include (1) forming lone pairs or pi bonds with electron deficient atoms or molecules, (2) moving pi bonds in aromatic structures, and (3) splitting pi bonds through photolysis. It also discusses determining hybridization of atoms based on the number of electron regions around them and writing condensed formulas.

1. Pushing electrons
a) Form a lone pair to an
electron deficient atom
H
CH 3O C
H
H
(CH 3)2N B
H
b) Form a π bond to an
electron deficient atom
H CH3
C C
CH2 CH3

2. Pushing electrons
c) From a lone pair to a π bond
H H
C C
O H
d) Move π bonds in aromatics
to generate equivalent
but not identical structures
CH3
CH 3

3. Pushing electrons
e) Divide electrons in a π bond
(note: single barb arrows “move”
one electron)
Cl - Cl hv 2 Cl
H
C O
H

4. Determine the hybridization of atoms
Hybrid orbitals make σ bonds and hold lone pairs not used in
resonance. If the atom has:
 4 electron regions: 4 bonds and/or lone pairs not involved in
resonance, hybridization is sp3
 3 electron regions: 3 bonds and/or lone pairs not involved in
resonance, hybridization is sp2
 2 electron regions: 2 bonds and/or lone pairs not involved in
resonance, hybridization is sp
H H
O
H H
H3C H
N
N N
H3C NH2

5. Write condensed formulas for each of the following and determine
the hybridization of each atom
N
C
F
B
F F

6. p orbitals make π bonds, hold lone pairs used in
resonance and are empty orbitals.
O
O
C C
N
O-

7. Draw a valid resonance structure for each of the
following and determine the hybridization of each atom
O
N
O
O
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