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FORMAL CHARGE AND
LEWIS DOT DIAGRAMS
FORMAL CHARGE AND LEWIS DOT DIAGRAMS

         Draw the Lewis Dot Diagram for SCN-




                                        -
                  S C N
                   6   +   4   + 5 + 1 = 16   electrons




But this isn’t the only possible way to draw the structure
FORMAL CHARGE AND LEWIS DOT DIAGRAMS

  Draw the 3 possible Lewis Dot Diagrams for SCN-

                                       -
                  S C N
                        -                                -
   S C N                         S C N

Which of these is the most likely resonance structure?
FORMAL CHARGE AND LEWIS DOT DIAGRAMS

Formal charges can be used to determine

1)which resonance structure is preferred over the
others when several resonance structures exist;
2)whether a particular structure is reasonable;
3)which part of a molecule is charged.



Formal Charge = Valence Electrons − (number of nonbonding electrons + number of bonds)




NOTE:
Formal charge is NOT the overall charge of a molecule.
Instead, they add up to the charge of a molecule.
FORMAL CHARGE AND LEWIS DOT DIAGRAMS
Assigning formal charges:
Formal Charge = Valence Electrons − (number of nonbonding electrons + number of bonds)


                              -1         0           0
                                                              -
                              S C N
 S: 6 - (6 + 1) = -1                                N: 5 - (2 + 3) = 0

                         C: 4 - (0 + 4) = 0
FORMAL CHARGE AND LEWIS DOT DIAGRAMS

 Assign formal charges to the other structures for SCN-
Formal Charge = Valence Electrons − (number of nonbonding electrons + number of bonds)


      +1           0          -2
                                        -          0           0          -1         -
       S C N                                        S C N
   S: 6 - (2 + 3) = +1                          S: 6 - (4 + 2) = 0
   C: 4 - (0 + 4) = 0                           C: 4 - (0 + 4) = 0
   N: 5 - (6 + 1) = -2                          N: 5 - (4 + 2) = -1
FORMAL CHARGE AND LEWIS DOT DIAGRAMS
Example #1: Compare the SCN- structures. Which one
       has the most neutral formal charges?

     +1      0      -2
                          -       0         0    -1     -
     S C N                        S C N
                    -1     0      0
                                        -
                    S C N
This is the most preferred structure. There are the most 0
formal charges and the most electronegative atom has the
                     negative charge.
FORMAL CHARGE AND LEWIS DOT DIAGRAMS
  Formal charges can also be used to determine if a
              structure is reasonable.

Example #2: Can SO2 have this Lewis structure?
                             0          0           0


                           O S O
                           Sulfur exceeds the octet


   O: 6 - (4 + 2) = 0                            ALL formal charges
                                                 are zero. Thus this
   S: 6 - (2 + 4) = 0                                structure is
                                                    reasonable.
Formal Charge = Valence Electrons − (number of nonbonding electrons + number of bonds)
FORMAL CHARGE AND LEWIS DOT DIAGRAMS
 Formal charges can also be used to determine if a
             structure is reasonable.

Example #2: Can SO2 have this Lewis structure?


          In fact, this structure is preferred
   0      0        0                0      +1     -1


  O S O                   vs
                                   O S O

Often it is preferred to violate the Octet Rule in order
to achieve a zero formal charge on an atom.
FORMAL CHARGE AND LEWIS DOT DIAGRAMS
 Furthermore, formal charges can be used to identify
         which part of a molecule is charged

Example #3: Which part of NO3- is charged?
         -1   -
   0
          +1



          -1
                                 The 2 single-bonded
O: 6 - (6 + 1) = -1              oxygen atoms have
                                 a negative charge,
O’: 6 - (4 + 2) = 0              and nitrogen has a
N: 5 - (0 + 4) = +1              positive charge.
FORMAL CHARGE AND LEWIS DOT DIAGRAMS
 Furthermore, formal charges can be used to identify
         which part of a molecule is charged

Example #3: Which part of NO3- is charged?
Why can’t NO3- be drawn this way so that the central atom does
not have a positive charge?
                               0
                     0

                              0



                                   -1
  Nitrogen cannot exceed the octet. Only elements beyond
  atomic number 10 (Neon) can exceed the Octet Rule.

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Tang 05 formal charge & lewis dot diagrams

  • 1. FORMAL CHARGE AND LEWIS DOT DIAGRAMS
  • 2. FORMAL CHARGE AND LEWIS DOT DIAGRAMS Draw the Lewis Dot Diagram for SCN- - S C N 6 + 4 + 5 + 1 = 16 electrons But this isn’t the only possible way to draw the structure
  • 3. FORMAL CHARGE AND LEWIS DOT DIAGRAMS Draw the 3 possible Lewis Dot Diagrams for SCN- - S C N - - S C N S C N Which of these is the most likely resonance structure?
  • 4. FORMAL CHARGE AND LEWIS DOT DIAGRAMS Formal charges can be used to determine 1)which resonance structure is preferred over the others when several resonance structures exist; 2)whether a particular structure is reasonable; 3)which part of a molecule is charged. Formal Charge = Valence Electrons − (number of nonbonding electrons + number of bonds) NOTE: Formal charge is NOT the overall charge of a molecule. Instead, they add up to the charge of a molecule.
  • 5. FORMAL CHARGE AND LEWIS DOT DIAGRAMS Assigning formal charges: Formal Charge = Valence Electrons − (number of nonbonding electrons + number of bonds) -1 0 0 - S C N S: 6 - (6 + 1) = -1 N: 5 - (2 + 3) = 0 C: 4 - (0 + 4) = 0
  • 6. FORMAL CHARGE AND LEWIS DOT DIAGRAMS Assign formal charges to the other structures for SCN- Formal Charge = Valence Electrons − (number of nonbonding electrons + number of bonds) +1 0 -2 - 0 0 -1 - S C N S C N S: 6 - (2 + 3) = +1 S: 6 - (4 + 2) = 0 C: 4 - (0 + 4) = 0 C: 4 - (0 + 4) = 0 N: 5 - (6 + 1) = -2 N: 5 - (4 + 2) = -1
  • 7. FORMAL CHARGE AND LEWIS DOT DIAGRAMS Example #1: Compare the SCN- structures. Which one has the most neutral formal charges? +1 0 -2 - 0 0 -1 - S C N S C N -1 0 0 - S C N This is the most preferred structure. There are the most 0 formal charges and the most electronegative atom has the negative charge.
  • 8. FORMAL CHARGE AND LEWIS DOT DIAGRAMS Formal charges can also be used to determine if a structure is reasonable. Example #2: Can SO2 have this Lewis structure? 0 0 0 O S O Sulfur exceeds the octet O: 6 - (4 + 2) = 0 ALL formal charges are zero. Thus this S: 6 - (2 + 4) = 0 structure is reasonable. Formal Charge = Valence Electrons − (number of nonbonding electrons + number of bonds)
  • 9. FORMAL CHARGE AND LEWIS DOT DIAGRAMS Formal charges can also be used to determine if a structure is reasonable. Example #2: Can SO2 have this Lewis structure? In fact, this structure is preferred 0 0 0 0 +1 -1 O S O vs O S O Often it is preferred to violate the Octet Rule in order to achieve a zero formal charge on an atom.
  • 10. FORMAL CHARGE AND LEWIS DOT DIAGRAMS Furthermore, formal charges can be used to identify which part of a molecule is charged Example #3: Which part of NO3- is charged? -1 - 0 +1 -1 The 2 single-bonded O: 6 - (6 + 1) = -1 oxygen atoms have a negative charge, O’: 6 - (4 + 2) = 0 and nitrogen has a N: 5 - (0 + 4) = +1 positive charge.
  • 11. FORMAL CHARGE AND LEWIS DOT DIAGRAMS Furthermore, formal charges can be used to identify which part of a molecule is charged Example #3: Which part of NO3- is charged? Why can’t NO3- be drawn this way so that the central atom does not have a positive charge? 0 0 0 -1 Nitrogen cannot exceed the octet. Only elements beyond atomic number 10 (Neon) can exceed the Octet Rule.