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Lecture One
Representing the Structures
of Organic Molecules
Why do we care?
The ability to make new molecules with
predictable structures and properties is one
aspect that sets organic chemistry apart from
other branches of chemistry, physics and
biology.
Functional Groups
Bonding
When do bonds form?
Bonds form when the interaction of
atoms lowers their net energy.
Now consider two cases for
bonding:
He , He vs. HeHe
lower E
higher E
NO BOND
H ,H vs. HH
higher E
lower E BOND
How do bonds form?
Ionic bonding is based on:
the transfer of electrons, which introduces
charge separation: My+ and Xn.
These new ions attract each other.
The energy of attraction is
E = the bonding energy
defined by Coulombs law.
k = the electrostatic force
Coulombs law: constant (a proportionality const.)
q1q2
____ q1, q2 = charges of the ions
E=k
r r = the distance separating
the ions
Covalent bonding
Electrostatic forces still apply
Electrons are shared
Orbital overlap replaces electron transfer
H O H
H O H H O H
O is like Ne H is like He
Covalent Bonding: CH4
First, write out all the atoms, each
with the proper # of electrons.
4 H C
Then pair one H
electron with each of
the C electrons.
The bonding pairs can
also be represented
H H
by single lines.
H C H H C H
H H
This type of representation is usually
called a Kekul structure.
Problem 1-2
Write the Lewis structure for each set of atoms.
Then figure out how they might bond together
covalently to form a stable compound.
a) C, Cl, Cl, F, H (central C atom)
b) N, 2 H, Cl (central N atom)
c) P and H (use as many H atoms as you need)
d) 2 C and 6 H
e) O, F, H (central O)
Multiple bonds
C2H4
In some molecules the atoms form double or triple bonds.
First, write out all the atoms
with the proper #s of electrons. C C H H H H
Second, join the two carbons
by forming one electron pair. (WHY?)
H C C H
Two electrons
H H remain unpaired!
Third, pair one H and
its electron with an
unpaired electron on Lets double check this.
one of the two Cs.
Multiple bonds
C2H4 Lets double check this.
...using a
C C H H H H different
method.
First, line up the atoms Second, add the Third, take the as
the way you expect electrons in pairs to yet unpaired
them to bond. make the bonds. electrons... and form a
second C-C bond.
H C C H H C C H H C C H
H H
H H H H
The pairings are The final structure
confirmed. is equivalent to:
HC CH
HC C H H C C H
Same as
HC CH
Acetylene
Problem 1-3
Draw the Lewis structure for each of the atoms
in the formulas below. Then draw the Lewis
structure for each molecule.
a) HCN (central C)
b) CH2O (central C)
c) C2Cl2
d) NHO (central N)
Lewis Structures of Ions
SO32
S O O O
OS O OS O OS O
O O
O
O S O
O
Cl
Cl P O
Cl
If we assign the
electrons:
Formal Charge
Some molecules dont seem to behave themselves
very well. for example :
PCl3O
Cl
7 valence electrons
Cl P +
O -
7 valence electrons 4 valence electrons 7 valence electrons
... not 5! ... not 6!
If we assign the
Cl
electrons: So P is positive,
7 valence electrons and O is negative.
Formal Charge
Some molecules dont seem to behave themselves
very well. for example :
PCl3O
Now if we reconstruct
the molecule:
and draw the bonding
Cl electron pairs as lines...
+ -
Cl P O and add the formal
Cl charges...
and remove the
we get a standard Kekul model, non-bonded
with formal charges. electrons...
Formal Charge
Features of formal charge:
They are not really full charges
Cl (but electron bookkeeping assigns
+ - them as full unit charges).
Cl P O
The sum of formal charges = the
Cl overall molecular/ionic charge.
Determination of formal charges
is required whenever any atom has
more or fewer than the typical
number of bonds.
Formal Charge (FC)
A formula for calculating formal charges:
Cl For P: FC = 5 1/2(8) 0 = +1
+ -
Cl P O
For O: FC = 6 1/2(2) 6 = 1
Cl [But feel free to do this without the formula!]
S O O O
O S O
Wheres the charge?
O
Problem 1-4:
Assign formal charges to SO32.
Problem 1-5
the two terminal oxygen
easily have drawn atoms are known to be
either of these:
O O O chemically equivalent.
Each of these two Lewis structures is valid, but neither can fully
represent the molecule. The solution is to call each a resonance
structure, and to state that the real structure is a hybrid:
O O O O O O
C C C
O O O O O
O
has two single bonds and one double bond.
The structure is easier to see if we write it as a
mixed Lewis/Kekul structure, with each bonding
electron pair represented by a single line.
It has three possible resonance structures.
The hybrid is the full set of resonance structures.
Locate the charges in each of the resonance structures.
What is the charge distribution in the actual molecule?
Models and Representations
An aside.
We have now seen two different structures
both said to represent ethene:
H C C H HC CH
H H H H
...and saw too that we needed to use three
different structures, each representing the
carbonate ion, somehow mixed together, to
represent the real structure of the ion.
NO3-
CO
CH3C(OH)CH3+
Lewis structures have
problems of their own:
exceptions to the octet rule.
Fewer than 8 electrons (BF3)
An odd number of electrons (NO)
More than 8 electrons (PCl5)
Fewer than 8 electrons: BF3
FBF The structure indicates that
there are only six electrons
around the boron atom.
F
H
FBF NH
F H
Cl
Problem 1-7