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, covalent and

hydrogen bonding.
 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.
 Covalent Bond

• A covalent bond is formed between two

non-metals that have similar
electronegativities.

• Neither atom is "strong" enough to

attract electrons from the other.
 Polar Covalent Bond
• In such a bond there is a charge separation
with one atom being slightly more positive
and the other more negative, i.e., the bond
will produce a dipole moment.

• The ability of an atom to attract electrons in

the presence of another atom is a
measurable property called
electronegativity.
 Hydrogen Bonding
• It is the electrostatic attraction between
two polar groups that occurs when
a hydrogen (H) atom covalently bound to a
highly electronegative atom such
as nitrogen (N), oxygen (O), or fluorine (F)
experiences the electrostatic field of
another highly electronegative atom nearby.

• It is an intermolecular force.
 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.
• 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 considered to be 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.
 Formal Charge
(reading assignment)

• It is the charge assigned to individual

atoms in a Lewis structure.

• Formula of calculation:

Number of
- No. of electrons
Formal charge = valence
an atom “owns”
electrons
• An atom “owns” all of its unshared
electrons and half its shared electrons.

C shares eight electrons.

C C ‘owns” four electrons.

Each C shares eight electrons.

C C Each C ‘owns” four electrons.

C shares six electrons.

C C has two unshared electrons.
C ‘owns” five electrons.
 • Calculation: Determine the formal charge
on each atom in the ion H3O+.

H O H
H
Step 1: Determine the no. of electron an
atom “owns”.

No. of electrons No. of unshared + (No. of shared

an atom “owns”
= electrons electrons)/2
 • No. of electrons “owned” by O atom

No. of electrons No. of unshared + (No. of shared

an atom “owns”
= electrons electrons)/2

= 2 + (6)/2
= 2 + [3]
=5
 • No. of electrons “owned” by each H atom

No. of electrons No. of unshared + (No. of shared

an atom “owns”
= electrons electrons)/2

= 0 + (2)/2
=1
 • Step 2: Calculate the formal charge.
Number of
No. of electrons
Formal charge = valence - an atom “owns”
electrons

• Formal charge of oxygen.

=6–5
= +1
• Formal charge of each hydrogen.
=1–1
=0

Therefore, the overall charge on the ion is

the sum of all of the formal charges:
=0+0+0+1
= +1
 Formal Charge Observed with Common
Bonding Patterns for C, N and O
Formal Charge
No. of valence
Atom +1 0 -1
electrons

C 4 C C C

N 5 N N N

O 6 O
O O
 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.
 Delocalization and Resonance
Structures Rules
• Resonance structures should have the
same number of electrons, do not add or
subtract any electrons. (check the number
of electrons by simply counting them).

• All resonance structures must follow the

rules of writing Lewis Structures.
• The hybridization of the structure must
stay the same.

• The skeleton of the structure can not be

changed (only the electrons move).

• Resonance structures must also have the

same amount of lone pairs.
 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.
• 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
 Electronic Structure of Atoms
• An atom contains of 10-10 m
nucleus made of N ucleus (proton s
neutron and and neutron s)
positively charged
protons. Sp ace occup ied
by electron s

• The larger
extranuclear space Proton
contain the N eutron
negatively charged 10-15 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.
 Molecular Orbitals (MO) Theory
(reading assignment)
• Molecular orbitals are obtained by
combining the atomic orbitals on the
atoms in the molecule.

• Chemical bonding occurs when the net

attractive forces between an electron and
two nuclei exceeds the electrostatic
repulsion between the two nuclei.
• For this to happen, the electron must be in
a region of space which is called the binding
region.
• Conversely, if the electron is off to one side,
in an anti-binding region, it actually adds to
the repulsion between the two nuclei and
helps push them away.
The Hydrogen Molecule Ion