CHAPTER 1

BONDING IN ORGANIC
COMPOUND
BY: Dr Nurziana
 Elements And Compounds
• An atom is the smallest particle that comprises a
chemical element.
• It consists of an electron cloud that surrounds a dense
nucleus. The cloud is made up of negatively charged
electrons.
• This nucleus contains positively charged protons and
electrically neutral neutrons,
• When the number of protons in the nucleus equals the
number of electrons, the atom is electrically neutral.
• An atom is classified according to its number of protons
and neutrons: the number of protons determines the
chemical element and the number of neutrons determines
the isotope of that element.
• A molecule is defined as group of at least two atoms in a
definite arrangement held together by very strong
chemical bonds .
 Electron Configuration
• Atomic number: the number of protons (or electrons) in
the nucleus. In other words, each element has a unique
number that identifies how many protons are in one atom
of that element.
• Mass number: the number protons and neutrons in its
atoms.
• Atomic mass: A total mass of protons, neutrons and
electrons in a single atom. Weighted average of an
element. Example: Isotopes of 81Br (35p + 46n) and 79Br
(35p+44n). So the atomic weight is 79.9
• Isotopes: Atoms of the same element can have different
numbers of neutrons; the different possible versions of
each element. So they have same atomic number but
different mass number.
• Example:
b) Atomic Orbitals
• Electrons are described as residing in
particular shells or energy level.
• Each shell has a certain capacity for
electrons. Electrons occupy specific atomic
orbitals.
• Atomic orbital – the space in which an
electron may be found around a single atom in
a particular state energy.
• The shape and geometric orientation of space
occupied by electrons are described by s, p, d
and f orbitals.
• An s orbital is spherical.

• The first electron shell is 1s and contain just

1s orbital.
• Second electron shell has two different kinds
of orbitals which are 2s and 2p.
• A p orbital has 2 lobes with the atom’s nucleus
located between the 2 lobes.
•Each shell except the first has 3 p orbitals (Px, Py and Pz)
identical in energy, size, shape and perpendicular to one another.
c) Filling Atomic Orbitals

AFBAU PRINCIPLE
- The atoms which have more than 1 electron, electrons are
placed in the lowest energetically available subshell. 
HUND’S RULE
-If two or more energetically equivalent orbitals are available
(e.g., p, d etc.) then electrons should be spread out before
they are paired up (Hund's rule).
d) Electron Configuration and Periodic Table

 Period 1: 1H and 2He – represent orderly completion of first

energy level and 1s orbital.
 Period 2: 3Li and 4Be complete the 2s orbital.
: 6 elements (B, C, N, O, F and Ne) the three p
orbitals are occupied.
 Period 3: the 3s (2 electrons, 2 elements) and 3p (6 electrons
6 elements) are being filled.
: It begins with 11Na (1s2 2s2 2p6 3s1) and ends with
18Ar (1s 2s 2p 3s 3p ).
2 2 6 2 6

 As a result, group I and II filling s orbitals, groups III to

VIII filling p orbitals.
 Elements within a particular group show similar chemical
properties.
 Stable Octets
• The octet rule states that atoms tend to combine in such a way that each
have eight electrons in their valence shells, giving them the same
electronic configuration as a noble gas (s2p6)
• Noble gases - eight electrons in the valence (outer most) shell (with the
exception of He which has two electrons).
• The rule is applicable to the main-group elements, especially carbon,
nitrogen, oxygen, and the halogens,
• Atoms can form stable electron configurations like noble gases by losing
electrons, gaining electrons and sharing electrons.
• Atoms that have 1, 2 or 3 electrons in their outer shells will tend to lose
them in interactions with atoms that have 5, 6 or 7 electrons in their
outer shells. Atoms that have 5, 6 or 7 electrons in their outer shells will
tend to gain electrons from atoms with 1, 2 or 3 electrons in their outer
shells.
• Atoms that have 4 electrons in the outer most energy level will tend
neither to totally lose nor totally gain electrons during interactions and
thus they tend to share electrons.
 Ionic (Electrovalent) Bonding
• An ionic bond (or electrovalent bond) is a type of chemical bond
that form between metal and non-metal ions. In short, it is a bond
formed by the attraction between two oppositely charged ions.
• In ionic bonding, metal atoms lose electrons and non-metal atoms 
gain electrons to form ions, which are then held together by
strong electrostatic interactions.  An ionic bond involves the
transfer of electrons. 
• The metal donates one or more electrons, forming a positively
charged ion or cation with a stable electron configuration. These
electrons then enter the non metal, causing it to form a negatively
charged ion or anion which also has a stable electron configuration.
• Ionic bonding will occur only if the overall energy change for the
reaction is favourable, the low electronegativity of metals and high
electronegativity of non-metals means that the energy change of
the reaction is most favorable when metals lose electrons and non-
metals gain electrons.
• The larger the difference in electronegativity between two
atoms, the more ionic the bond.
• Electronegativity – Is a measure of the tendency of an atom
to attract a bonding pair of electrons
 2.8.1 2.8

2.8.7
2.8.8

[   ]+ [ ]-
 Covalent Bonding
• Covalent bonding- involve the sharing of electron pairs
between atoms.
• Each atom donates half of the electrons to be shared
• covalent bonding does not necessarily require the two atoms
be of the same elements, only that they be of comparable
electronegativity.
• To depict covalent bonds in molecules : Lewis dot Structure
and line bond formula
• To draw an electrons dot formula (Lewis dot structures) of the
organic compound (example: CH4)
1) determine the number of electrons available for the formula

2) Hydrogen is in column IA and thus has 1 electron. Since there

are 4 hydrogen atoms, the total for hydrogen will be 4
electrons.
Carbon is in column IVA and thus has 4 outer electrons...

3) determine which atom will be in the center of the molecule.

Hydrogen atoms are only able to form one bond to other atoms so
we need to put the carbon atom in the center.

4) draw all of the other hydrogen atoms around the carbon atom
and place 2 electrons between these hydrogen atoms and the
carbon atom. This gives you a total of 8 electrons.
Electron structures involving multiple bonds

Multiple equivalent structures: resonance

• Polyatomic Ions and Formal Charge
-polyatomic ion – is a charged species
composed of two or more atoms covalently
bonded.
nitrate NO3 -1 chromate CrO4 -2 chlorate ClO3 -1 dichromate Cr2O7 -2
sulfate SO4 -2 phosphate PO4 -3 carbonate CO3 -2 acetate C2H3O2 -1
hydroxide OH -1
cyanide CN -1
ammonium NH4 +1    

Formal charge- The formal charge on an atom is the

electric charge it would have if all bonding electrons were
shared equally with its bonded neighbors.
-is a accounting procedure to determine the location of charge
in a molecule as well as compare how good Lewis structure might
be.
FC = GN - UE -1/2BE
FC = Formal charge
GN =Periodic table group number (number of
valence electrons in free)
UE = number of unshared electrons
BE = number of electrons shared in covalent bonds.

To calculate the formal charge on nitrogen there are three pieces of information that you
need to know:
• the group number (number of valence electrons), the number of non-bonding electrons, and the
number of shared electrons. Nitrogen is in group five; thus, it has five valence electrons
• Number of non-bonding electrons: there are no non-bonding electrons, so this is zero
• Number of shared electrons: there are four bonds, and there are two electrons in each bond,
so this number is eight
formal charge = 5 - 0 - 0.5(8) = +1
Thus, the nitrogen has a formal charge of +1
• Polar bonds: Is a covalent bond in which
there is a separation of charge between 2
atoms – one atom is slightly positive and
the other is slightly negative. Example: HCl
 An Orbital Approach to
Covalent Bonding
• How are electrons shared to form covalent bonds?
Overlapping the atomic orbitals.
• Sigma, σ bond is formed head to head overlap of atomic
orbital in one position
• Pi, π bond is formed when parallel p orbitals each with one
electron overlap in two positions.

Sigma, σ bond Pi, π bond

• Electron configuration for carbon: carbon
has 4 electrons in its outer shell 2s2 2px1
2py1
• Carbon tetravalence is explained by
exciting one 2s electron to a 2p orbital –
creating 4 unpaired electrons during
bonding.
• Shapes of organic molecules – atoms are
oriented in a molecule so that the
repulsion between the electron pair
(bonding or nonbonding) around an atom is
minimized.
• Carbon will have 4, 3 and 2 atoms bonded
to it.
Carbon bonded to 4 atoms
• Example: methane, CH4.
• To satisfy the valence of all 5 atoms, each of H must be
bonded to the carbon by a single bond.
• The hydrogen must be put at maximum distances from one
another to reach most stable molecular geometry.
• 1s orbital (H atom) and 2s 2px 2py 2pz (C atom is in excited
state) are hybridized (blend) to form 4 new orbitals that
are equivalent and at the ideal 109.5o angle from one
another
• The new sp3 hybrid orbitals are formed, composed from 1s
and three p orbitals.
• The geometry formed is tetrahedron.
• 4 sigma bonds were formed.
Carbon bonded to 3 atoms
• Example: Ethylene, CH2=CH2
• Central atom, C is bonded to three atoms and the possible
arrangement that allows three atoms bonded to a central
carbon is trigonal with the angle of 120o.
• The outer shell must be hybridized to create an orbital
geometry consistent with the preferred trigonal shape.
• Only 3 orbitals have to be hybridized, where s and two p
orbitals are combined to form a new sp2 hybrid orbitals.
• These sp2 orbitals are directed towards the corner of an
equilateral triangle.
• An unhybridized p orbital remains unchanged on each
carbon, perpendicular to the hybridized orbitals whose axes
all lie in one plane.
• Overlap of two sp2 hybrid orbitals of carbons forming a sp2
-sp2 σ bond
• The unhybridized p orbitals of carbons are parallel to each
other, both lobes of that p orbitals merge above and below
σ bond forming p-p π bond. As a result, carbon-carbon
double bond is composed from a σ bond and a π bond.
• The s-sp2 σ bonds are also formed by overlapping each
remaining sp2 hybrid orbitals of the carbons with a
spherical s orbital of a hydrogen.
Carbon bonded to 2 atoms
• Example : acetylene CHΞCH
• The bonded atoms are on opposite sides of the central
carbon at a maximum distances in a linear geometry of 180o
bond angles.
• A carbon 2s orbital hybridizes with only a single p orbital
resulting sp hybrid orbitals and two p orbitals remain
unchanged.
• When sp hybridized carbon atoms approach each other, the
hybrid orbital overlap head on to form strong sp-sp σ bond,
the 2 unhybridized p orbitals of carbons form 2 p-p π bonds
resulting formation of carbon-carbon triple bonds.
• A spherical s orbital of hydrogen hybridizes with the
remaining 2p orbital of carbon to form s-sp σ bond to
complete the acetylene molecule.
HYBRIDIZATION OF OTHER ATOM: NITROGEN AND
OXYGEN
Oxygen has 2 pairs nonbonding electrons.

O has double bond and 2 pairs

 O has 2 single bonds & 2 pairs of
nonbonding electrons.
nonbonding electrons – four space The O is sp2 hybridized, two of
occupying group – O is sp3
three sp2 orbitals occupied by
hybridized
nonbonding electrons pairs
2 orbitals have one electron each
The remaining sp2 orbital and
and overlap with orbitals from C and
unhybridized orbital overlap each
H to form a σ bonds.
other to form σ and π double bond.
• Nitrogen has one pair nonbonding electrons. So the atom can have
3 (sp3), 2 (sp2)or 1 (sp) bonded atoms.