CHAPTER 1

Carbon Compounds and

Chemical Bonds
 Carbon Compounds
• Carbon is one of the most versatile
elements in the periodic table.

• It is unique that its atoms can form stable

covalent bonds with each other and with
atoms of other elements in a multitude of
variations.
 Chemical Bonds
• It is the joining of two atoms in a stable
arrangement. Joining two or more
elements form compounds.

• Bonding may occur between the atoms of

the same or different elements.

• Types of bonding; ionic and covalent

bonds.
 Ionic Bond
• An ionic bond is formed between a metal
and a non-metal.

• Non-metals (-ve ion) are "stronger" than

the metal (+ve ion) and can get electrons
very easily from the metal.

• These two opposite ions attract each other

and form the ionic bond.
Metal Lost e- Non-metal
gained e-
 Covalent Bond
• A covalent bond is formed when pairs of
electron are shared between two non-metals
that have similar electronegativities, which
need to gain electrons to get a stable octet
of electrons or a filled outer shell.
 Types of Covalent Bonds
Bonds can be described by the difference in the
electronegativity of the bonding atoms.

Two types of covalent bonds occur in molecules:

• nonpolar covalent bonds; bonding electrons
are shared equally
• polar covalent bonds; bonding electrons are
shared unequally
 Nonpolar Covalent Bonds
A nonpolar covalent bond between nonmetal
atoms
• consists of an equal (or almost equal) sharing of
electrons
• has a zero (or close to zero) electronegativity
difference (0.0 to 0.4)
Non-Polar Molecule

Cl Cl
Equal Sharing of Electrons
12
 Polar Covalent Bonds
A polar covalent bond between nonmetal atoms
• consists of an unequal sharing of electrons
• has an electronegativity difference of 0.5 to
1.9
 Polar Molecule

+
H Cl -
More
electronegativity

Unequal Sharing of Electrons

14
 Polar and Nonpolar Covalent
Bonds

Figure 10.2 In the nonpolar covalent bond of H2, electrons are

shared equally. In the polar covalent bond of HCl, electrons are
shared unequally.
 Water is a POLAR molecule

ANY time there are unshared pairs

of electrons on the central atom,
the molecule is POLAR
H H
O
16
 Electronegativity and Polarity
• Electronegativity is a measure of an atom's attraction
for electron in a bond.
• When comparing two different elements,
one is more electronegative than the
other if it attracts electron density
towards itself.

• One is less electronegative or more

electropositive if it gives up electron
density to the other element. (e.g NaCl)
• The greater the electronegativity difference,
the more ionic the bond is.

• Bonds that are partly ionic are called

polar covalent bonds.

• Nonpolar covalent bonds, with equal

sharing of the bond electrons, arise when
the electronegativities of the two atoms are
equal.
• Example:
2.5 2.2
2.5

C C C H

nonpolar bond nonpolar bond

• C-H bonds are nonpolar because the

electronegativity difference between C
and hydrogen is small.
• For C-O bond, the electron are pulled away
from C (2.6 refer to Periodic Table) toward
O (3.4), the element of higher
electronegativity. The bond is polar.

• The bond has a separation of charge a.k.a

dipole.
C is electron deficient O is electron rich

δ+ δ-
C O
• Usually for a polar bond the
electronegativity difference between two
atoms is ≥ 0.5 units.

• Conclusion: Electronegativity differences of

less than 0.5 result in nonpolar covalent
bonds; differences up to 1.9 polar covalent
bonds and differences of 2 or more
indicate ionic bonds.
 Solution
Determine if the molecule OF2 is polar or
nonpolar.
Step 1 Determine if the bonds are polar or
nonpolar covalent.
Oxygen has an electronegativity of 3.5,
and fluorine has an electronegativity of
4.0. O—F bonds are polar covalent.
 Solution
Determine if the molecule OF2 is polar or
nonpolar.
Step 2 If the bonds are polar covalent, draw
the electron-dot formula and determine if the
dipoles cancel.
Dipoles in O—F bonds do not cancel;
the molecule is polar. Furthermore, it has a bent
molecular geometry and unshared electron. .
 Polarity of Molecules—Nonpolar
• A nonpolar molecule also occurs when polar bonds (dipoles)
cancel each other because of a symmetrical arrangement.
• Molecules such as CO2 and CCl4 contain polar bonds with dipoles
that cancel each other out. There are no positive or negative poles
formed in the molecule. Nonpolar molecules are generally
symmetrical, like the tetrahedral molecule carbon tetrachloride.
Another example is boron trifluoride, which is trigonal planar. In
symmetrical molecules, the dipole charges cancel out.
 Polarity of Molecules—Polar

• A polar molecule occurs when the dipoles from

individual bonds do not cancel each other out.

• For molecules with two or more electron groups,

the shape (such as bent or trigonal pyramidal)
determines whether the dipoles cancel.
 Polarity of Molecules—Polar
Examples of polar molecules include HCl, H2O, and
NH3.
• HCl is linear and contains a polar bond.

• H2O is bent and contains two polar bonds as well

as two lone pairs on oxygen.
 Polarity of Molecules—Polar

• NH3 is trigonal pyramidal and contains three

polar bonds and a lone pair on nitrogen.
 Non-polar Polar
• symmetrical arrangement (can cancel • Unsymmetrical arrangement (dipole
each other). cannot cancel)
H2O has a bent
Dipole (crossed arrow with shape, and it is
direction) from carbon non-symmetrical
center (charge +ve) to Cl molecule. More of
(charge –ve). The structure the electrons are
is symmetry , therefore, attracted to the
the net dipole moment is oxygen atoms,
zero or zero net charge resulting in a net
(the charge is distributed charge.
equally between atoms). Furthermore, it
has unshared
electrons.

• Shape: tetrahedral and trigonal planar • H2O is a polar molecule.

• Shape: linear, bent, trigonal pyramidal.

A simple way to determine between polar and

non-polar molecule it to draw the structure. Then
you can see the shared/unshared electron.
 Formal Charge

• It is the charge assigned to individual

atoms in a Lewis structure.
 Resonance
• Resonance structures are two forms of a
molecule where the chemical connectivity
is the same BUT the electrons are
distributed differently around the structure.

• The electrons are able to move to help

stabilize the molecule. This movement of
the electrons is called delocalization.
Resonance
• What if more than one
valid Lewis dot structure
is possible?
• Consider Nitrate ion.
• Nitrogen bound to 3
oxygen atoms, one with a
double bond.
• But is that the only
possible structure that
obeys the octet rule?
The Difference Between Delocalized
and Localized Electrons
 Lewis Structures
• It is the electron dot representations for
molecules to show the connection among
atoms and the placement of unshared
valence electrons (lone pairs).

All atoms are surrounded by 8 electrons, fulfilling

the octet rule.
 No. of bonds No. of non-bonded
electron pairs

1 0
H
4 0

3 1
N
 No. of bonds No. of non-bonded
electron pairs

2 2
O
1 3

X
 Hybridization

• Covalent bonds are formed when atomic

orbitals overlap. There are two types of
orbital overlap.

• Sigma, σ, overlap occurs when there is

one bonding interaction that results from
the overlap of two orbitals.
 Valence Bond Theory
• Hybridization is a major player in this
approach to bonding.
• There are two ways orbitals can overlap to
form bonds between atoms.
 Sigma () Bonds

• Sigma bonds are characterized by

– Head-to-head overlap.
– Cylindrical symmetry of electron density about
the internuclear axis.
 Pi () Bonds

• Pi bonds are characterized by

– Side-to-side overlap.
– Electron density above and below the
internuclear axis.
 Single Bonds

Single bonds are always  bonds,

because  overlap is greater,
resulting in a stronger bond and
more energy lowering.
 Multiple Bonds

In a multiple bond, one of the

bonds is a  bond and the rest
are  bonds.
Orbital overlaps involved in  bonds of methane
Figure 1.22

Francis A. Carey, Organic Chemistry,

Fourth Edition. Copyright © 2000 The
McGraw-Hill Companies, Inc. All rights
reserved.
• Pi, π, overlap occurs when two bonding
interactions result from the overlap of
orbitals.

• Orbital overlaps relate to the type of

bonding that is occurring between
atoms:
single bond σ overlap
double bond σ and π overlaps
triple bond σ and two π overlaps
 Bonding in Organic Compounds
Number of atoms bonded to central carbon
4 3 2
H H H H
Example H C C H H H C C H
C C H
H H
Hybridization sp3 sp2 sp
Geometry Tetrahedral Trigonal Linear
planar
Bond angle 109.5° 120° 180°
Molecular 4σ 3σ, 1π 2σ, 2π
Orbital
Atoms of ethylene
Figure 1.24

Francis A. Carey, Organic Chemistry,

Fourth Edition. Copyright © 2000 The
McGraw-Hill Companies, Inc. All rights
reserved.
Acetylene is a linear molecule
Figure 1.28

Francis A. Carey, Organic Chemistry,

Fourth Edition. Copyright © 2000 The
McGraw-Hill Companies, Inc. All rights
reserved.
 5 Geometrical Shapes of Molecules
a) Tetrahedral
Ball and stick Molecule geometry
model

Shared Pairs /No. of electron = 4

51
Unshared Pairs = 0
b) Trigonal Planar
Ball and stick
model

Molecule geometry X
A
X X
Shared Pairs /No. of electron = 3
Unshared Pairs = 0
 c) Linear (straight line)
Ball and stick OR
model

Molecule geometry X A X
OR

A X
Shared Pairs /No. of electron = 2
Unshared Pairs = 0
d) Bent
Ball and stick
model

..
Lewis Diagram A
X X
Shared Pairs/No. of electron = 2
Unshared Pairs = 1 or 2 54
e) Trigonal Pyramidal
Ball and stick Molecule geometry
model

Shared Pairs /No. of electron = 3

Unshared Pairs = 1 55
 (e.g. CO2)

(e.g. BCl3) (e.g. SO2)

(e.g. CH4)
(e.g. NH3) (e.g. H2O)
 Electronic Structure of Atoms
• An atom contains of 10 -1 0
m
nucleus made of N u c le u s (p ro to n s
neutron and a n d n e u tro n s)
positively charged
protons. S p a ce o ccu p ie d
b y e le ctro n s

• The larger
extranuclear space P ro to n
contain the N e u tro n
negatively charged 10 -1 5
m
electrons.
• Electrons do not move
freely in the space around a
nucleus but rather confined
to regions of space called
principal energy levels or
shells.

• The shells can be numbered

as 1st, 2nd, 3rd and 4th from
the inside out.

• Each shell contain 2n2

electrons; and n is the nucleus

number of shell.
• The first shell can hold 2 electrons, the second
8 electrons, the third 18 and the fourth 32.

• Table: Distribution of electrons in shells

Shell Electron capacity Relative energies of
2n2 electrons in each
shell
4 2(4)2 = 32 Higher
3 2(3)2 = 18
2 2(2)2 = 8
1 2(1)2 = 2 lower
• The electrons in the first shell are lowest in
energy because they are nearest to the
positively charged nucleus and are held
most strongly by it.

• The farther a shell is from the nucleus, the

larger it is, the more electron it can hold;
and the higher energies of those electrons.
• Shells are divided into subshells designated
by the letters s, p, d and f. The number of
subshells in a given shell is equal to the
shell number; for example; shell no.3 has 3
subshells.

• Electrons are group in orbitals within these

shells.

• An orbital is a region of space that can hold

2 electrons.
• The second shell contain one 2s orbital and
three 2p orbitals. All p orbitals come in sets
of three and can hold up to 6 electrons.

• The third shell contain one 3s orbital, 3p

orbitals and five 3d orbitals. All d orbitals
come in set of five and can hold up to 10
electrons.

• All of f orbitals come in set of seven and

can hold up to 14 electrons.
 Table: Distribution of orbitals within shells.
Shell Orbitals contained in Maximum
each shell number of
electrons shell
can hold
4 One 4s, three 4p, five 4d 2 + 6 + 10 + 14 =
and seven 4f 32
3 One 3s, three 3p and 2 + 6 + 10 = 18
five 3d
2 One 2s, three 2p 2+6=8
1 One 1s 2
Electron distribution in atoms

Shell
1 2 3 4
number
Subshell
s s, p s, p, d s, p, d, f
designation
# of orbitals 1 1, 3 1, 3, 5 1, 3, 5, 7
# of
2 2, 6 2, 6, 10 2, 6, 10, 14
electrons
Total
electron 2 8 18 32
capacity
• Electron configuration of atoms describe how
electrons occupy in orbitals.
 Valence Electron
• The electrons of an atom that participate
in the formation of chemical bonds with
other atoms. It determines the properties
of a given element.
• For example, carbon in group 4A has four
valence electron and oxygen in group 6A
has six.
 Intermolecular Forces
• Intramolecular forces are the forces within a
molecule or ionic compound.
• Intermolecular forces are the forces between
molecules or ions and molecules.

Intramolecular forces Intermolecular forces

 Strength
Intramolecular bonds > intermolecular forces

Intramolecular bonds are stronger because it

would take a lot more energy to overcome
covalent bonds and break apart the molecule
than to overcome intermolecular forces in
between the atoms (to make it become a liquid or
gas).
 Intermolecular Forces

The attractions between molecules are not nearly

as strong as the intramolecular attractions that
hold compounds together.
 Intermolecular Forces

These intermolecular attractions are, however,

strong enough to control physical properties, such
as boiling and melting points, vapor pressures,
and viscosities.
 Summary Intermolecular Forces

Dipole-dipole Interactions

*Example: HCl
 The 4 Intermolecular forces
• London dispersion forces
• Dipole–dipole interactions
• Hydrogen bonding
• Ion-Dipole interactions
 Dipole–Dipole Interactions
– WEAK intermolecular force
– Bonds have high electronegativity differences forming
polar covalent molecules, but not as high as those that
result in hydrogen bonding. 0.21<EN<1.99

• Molecules that have permanent dipoles are attracted to

each other.
– Partial negative and partial positive charges slightly
attracted to each other.
– These forces are only important when the molecules are
close to each other.
– Only occur between polar covalent molecules.
 Dipole–Dipole Interactions

The more polar the molecule, the higher its

boiling point.
78

DIPOLE-DIPOLE FORCES
• Molecules with larger dipole
moments have higher
melting and boiling points
(hard to break) than those
with small dipole moments.

• Dipole attractions are

relatively weak and tend to
be liquids or gas at room
temperature.
Dipole-Dipole Interactions

79
 Hydrogen Bonding

• The dipole–dipole
interactions experienced
when H is bonded to N, O, or
F are unusually strong.
• We call these interactions
hydrogen bonds.
 Hydrogen Bonding
• Hydrogen bonding arises
in part from the high
electronegativity of
nitrogen, oxygen, and
fluorine.

Also, when hydrogen is bonded to one of those

very electronegative elements, the hydrogen
nucleus is exposed.
Which substance has the highest
boiling point?
• HF The H-F bond has the highest
• NH3 electronegativity difference
SO
• CO2
HF has the most polar bond
• WHY?
resulting in the strongest H
bonding (and therefore needs the
most energy to overcome the
intermolecular forces and boil)
82