Introduction To Organic Chemistry: of Chemical Bonding Fundamentals

CHAPTER 1
INTRODUCTION TO ORGANIC CHEMISTRY

1.1 Review of chemical bonding fundamentals
Atoms try to achieve an s2p6 electron configuration (full outer valence shell,
stable octet).
They can do this by forming

a) covalent bonds (sharing electrons equally),
b) polar covalent bonds (sharing electrons unequally) or
c) ionic bonds (losing or gaining electrons).
One can determine the type of bond formed between 2 atoms by comparing
the electronegativity values of the 2 atoms. Electronegativity is a number
between 1.0 and 4.0 that indicates how strongly an atom attracts electrons.
Atoms on the left hand side of the periodic table have low values of
electronegativity (less than 2.0) and atoms on the right hand side of the
periodic table have higher values of electronegativity.
A difference more than or equal to 2.0 is an ionic bond

A difference between 0.4 and 2.0 is a polar covalent bond.
A difference in electronegativity less than or equal to 0.4 is a covalent bond.
The electronegativity of the atoms we will be dealing with this term:
H = 2.2; C = 2.6; O = 3.5; N = 3.1; F = 4.0; Cl = 3.2; S = 2.6; Br = 2.9;

I=2.7
2
KNOW:
Covalent (non-polar): C-C, C-H, C-S, S-H
Moderately polar: C-Cl
Polar: O-H, N-H, C-N, C-O
Bonding in molecules is conveniently shown using Lewis dot diagrams

which show the number of electrons in their outer shell.
IA IIA IIIA IVA VA VIA VIIA Noble Gases

H· He :
· · · · ..
Li · · Be · ·B· ·C· :N· :O· :F: : Ne :
. .. .. ..
· ·
..
· · · ·
Na · · Mg · · Al · · Si · :P· :S· : Cl : : Ar :
. . . .. .. ..
. ..
K· · Ca · : Br : : Kr :
.. ..
. ..
Rb · · Sr · :I: : Xe :
.. ..
Cs · · Ba ·
Know the Lewis dot structures of the highlighted atoms.
Bonding examples using Lewis dot:

.. .. .. .. .. ..
______
2 F atoms : F· +·F: > : F : F : or : F - F :
.. .. .. .. .. ..
Review of s and p orbital shapes:
3
s orbital p orbital
Orbital overlap view:
F (atomic # 9) 1s22s 22p5
F 1s22s 22p5
Each F atom is one electron short of a full outer shell. It can fill that unfilled
p orbital by overlapping the unpaired electron of one F atom with the
unpaired electron (with opposite spin) of a second F atom.
The resulting bond has its electron density concentrated on the line
between the two F nuclei and is called a sigma bond.
Lewis dot notation for molecules containing O atoms:
a)H2O
.. ·H δ- . . δ+
______
:O· + > : O___ H
.
·H δ+ H
The arrows indicate the dipoles: the direction in which the highest shared
electron density occurs in the bond.
There are particularly strong attractions between the δ on the O of one
-
water molecule and the δ+ on the H atom of another water

molecule. These attractions are called hydrogen bonds. They are
very important attractions not only in water but in proteins,
4
carbohydrates, and nucleic acids. Hydrogen bonds are a specific
type of polar attraction between a H with a δ+ and a very
electronegative atom F, O, or N.
Modified from Wikipedia

b) Do the Lewis dot diagram for H2O2.
loldamn.com
b) O2
.. .. .. ..
___
:O · + ·O: > O=O
5
. . .. ..
The result is a double covalent bond with 4 shared electrons (2 pairs).
Orbital overlap representation of O2 :

O: 1s22s22p4
The 2 electrons in the pi orbital are not as close to the two positively charged
O nuclei and can more easily react with another atom or especially a
positively charged ion. In general pi electrons of a double bond will be more
reactive than the sigma bond.
In both molecules above O atom forms two bonds, either two single bonds
or one double bond
Lewis dot structures of molecules with N atoms
6
This produces a triple covalent bond with 6 shared electrons (3 pairs).
In all of the above molecules the 3 unpaired electrons of N form 3 bonds: 3

single bonds, a double and a single, or a triple bond.
What will the orbital overlap picture of N2 look like?
7
Lewis dot structures for molecules with C atoms
C is in Group IV and it forms 4 bonds:
CH4 C2H6 C3H8 C4H10
Since H is the most common atom found bonding with C we will sometimes
simply show 4 bonds coming off of a C without explicitly showing the atom
at the end of the bond. When we do this, it is assumed that H is the atom
bonded. If some other atom beside H is bonded to C, we HAVE to show it
explicitly.
These chains can be almost infinitely long and these long chains are what
make the chemistry of carbon so extensive and so diverse.

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CHAPTER 1

INTRODUCTION TO ORGANIC CHEMISTRY

They can do this by forming

A difference more than or equal to 2.0 is an ionic bond

The electronegativity of the atoms we will be dealing with this term:

H = 2.2; C = 2.6; O = 3.5; N = 3.1; F = 4.0; Cl = 3.2; S = 2.6; Br = 2.9;

Bonding in molecules is conveniently shown using Lewis dot diagrams

IA IIA IIIA IVA VA VIA VIIA Noble Gases

Know the Lewis dot structures of the highlighted atoms.

Bonding examples using Lewis dot:

Review of s and p orbital shapes:

Orbital overlap view:

F (atomic # 9) 1s22s 22p5

Lewis dot notation for molecules containing O atoms:

water molecule and the δ+ on the H atom of another water

Modified from Wikipedia

The result is a double covalent bond with 4 shared electrons (2 pairs).

Orbital overlap representation of O2 :

Lewis dot structures of molecules with N atoms

In all of the above molecules the 3 unpaired electrons of N form 3 bonds: 3

What will the orbital overlap picture of N2 look like?

C is in Group IV and it forms 4 bonds:

CH4 C2H6 C3H8 C4H10

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