COVENANT UNIVERSITY,

CST DEPARTMENT OF
CHEMISTRY
COURSE: CHM122 (CCMAS)
CHM121,123
(BMAS)
SEMESTER: OMEGA
2023/2024
LECTURER: PROF. AJANI O.O.
OVERVIEW OF THIS MODULE
At the end of this module, learner
should be able to:
Detect elemental composition in organic
compounds
Determine structure of organic
compounds
Differentiate btw ionic & covalent bond
Have clarity on hybridization concept
2
 ELEMENTAL COMPOSITION
Detection of Carbon and Hydrogen
Principle: Carbon and hydrogen are
detected by heating the organic compound
with cupric oxide (CuO) strongly, where
carbon is oxidized to carbon (IV) oxide &
hydrogen to water. CO2 is tested by lime
water, whereas water is tested by
anhydrous copper sulphate test.
3
C + 2CuO CO2 + 2Cu
H2 + CuO H2O + Cu 4
Detection of Nitrogen,
Sulphur, & Halogen: Lassaigne
Na Fusion Test
N, S and halogen in the organic
compds, should be converted into
their ionic forms.

5
Confirmation of N: Prussian Blue

6
Confirmation of S: Black ppt.
+
H
(CH3COO)2Pb
+ Na 2S PbS + 2CH3COOH
Lead acetate in sodium black
extract precipitate

7
 Confirmation of Halide: Coloured ppt.

AgNO3 + NaX HNO3 AgX + 3

NaNO
coloured ppt
white precipitate and readily soluble in aq. ammonia- Cl confirmed
Pale yellow ppt. & slightly less soluble in aq. ammonia -Br confirmed
Yellow ppt. and insoluble in aq. ammonia - I confirmed
8
 STRUCTURAL DETERMINATION
METHODS (1/3)
Structure and identity of organic
compounds can be determined using
three methods, they are:
1.Physical Method
2.Chemical Method and
3.Spectroscopic Method

9
 STRUCTURAL DETERMINATION
METHODS (2/3)
1. Physical Method: This involves
the use of physical properties of an
organic compound for structural
characterization such properties
are colour, melting and boiling
points, refractive index, density,
2. Chemical Method: This entails
the use of chemical behavior and
tests to identify the nature of
functional groups in acompound 10
 STRUCTURAL DETERMINATION
METHODS (3/3)

3. Spectroscopic Method: It
involves the use of instrumentation
technique to authenticate the
identity and structure of an organic
molecule. Spectroscopic technique
examples involves the use of
Infrared (IR), Ultraviolet-Visible
(UV-Vis), X-ray Diffraction (XRD),
Scanning Electron Microscope 11
 IONIC AND COVALENT BONDING
Ionic Bonding: is complete
transfer of valence electron(s) btw
atoms. MgCl2, NaCl, KBr, CaO.

Covalent bonding: is the sharing

of electrons btw atoms. PCl3, HCl,
H2 , Cl2, CH4, SF4, C2H4
12
IONIC VS COVALENT COMPOUNDS
 HYBRIDIZATION
Hybridization: can be defined
as the blending of two or more
atomic orbitals of different
energy to obtain a hybrid orbital
of equivalent energy level.
It helps us to know the molecular
geometry of the compounds,
type of bond, their bond angles,
the nature of electron pair [i.e.
number of Bond Pair (BP), Lone 14
 Determination of the
Pattern
(i). Write out the ground state (GS)
valence electronic configuration of
central atom. Promote the excited
state (ES) in such a way to
accommodate electrons from
surrounding groups or atoms.
(ii). Pair each electron from the
surrounding atoms with each half-
filled suborbital level of the central
atom to have fully filled configrn. at
each suborbital level.
(iii). Write out the valence suborbital 15
Hybridization Pattern of
SF4
• Central atom is Sulphur (16S)
with G.S. electronic
configuration of 1s2 2s2 2p6 3s2
3p4

• G.S. valence electronic

configuration Ex. State valence
electronic conf.
16
Sub-Orbital Determination of
SF4
2 4
3s 3p
V.E.C. of S in GS

2 3 1
3s 3p 3d
V.E.C. of S in ES

Config. of SF4
3 3
s + p + d = sp d
17
 Solution via Long Method
3
Hybrid. Pattern of SF4 = sp d (with 4BP + 1LP = 5TP).
o o
Shape is Trig. Pyramid bond angle of 90 and 120
F
F
S F
F

18
 Short Method of
Determination
Val electron of S + Total no of Fluorine 6+4 10
TP = = = = 5
2 2 2
3
Hybrid. Pattern of SF4 = sp d
F
(with 4BP + 1LP = 5TP).
F
Shape is Trig. Pyramid S F
o o F
bond angle of 90 and 120

19
Total No of No of Hybri Geometrical Ideal Typica
Electron Bond Lone d Distribution Bond l
Pair Pairs Pairs orbita or Shape Angle Examp
(BP) (LP) l le
2 2 0 sp Linear 180O BeCl2
3 3 0 sp2 Trig. Planar 120O BF3
3 2 1 sp2 Trig. Planar 120O SiO2
4 4 0 sp3 Tetrahedral 109.5o CH4
4 3 1 sp3 Trig. 107 o NH3
4 2 2 sp3 Pyramid 104.5 o H2O
Angular/
Bent
5 5 0 sp3d Trig.Bipyra 90o, PCl5
5 4 1 sp3d m 120o SF4
5 3 2 sp3d Trig. 90o, ClF3
5 2 3 sp3d Pyramid 120o
XeF2
Trig. Planar 120o
o 20
 Hybridization in Carbon
3 3
2s + 2p Four of sp hybrid orbitals.
2 2
2s + 2p Three of sp hybrid orbitals.
2s + 2p Two of sp hybrid orbitals.

21
 sp3 Hybridization in
Carbon
2s orbital mixed with three 2p (i.e.
2px, 2py and 2pz) orbitals to form
four sp3 hybrid orbitals of
equivalent energy which are
tetrahedrally arranged (to W
minimize repulsion) with d
bond angle (B.A.) of 109.5o. C
X Y Z
22
 Energy Level Diagram

Energy PX PY PZ
after blending 3 SP3 3 3
SP SP SP
3
sp hybrid
S S state of C.
G.S. Val. of Carbon E.S. Val. of Carbon
2s2 2p2

Orbital Blending Diagram

+ + +
23
A Typical sp 3 Hybridizn. In
CH4
Each of the half-filled four sp3
hybrid orbital can use bigger side
of its lode to overlap with each 1s
orbital of hydrogen to form 4
bonds in methane.
H
c
H H
H
Orbital picture 3-D Structure
24
Carbon
2s orbital mixed with two of its
2p (i.e. 2px, 2py) orbitals to obtain
three sp2 hybrid orbitals of
equivalent energy with trigonal
planar arrangement having bond
angle of 120o. Here, the third 2p
orbital (i.e. 2pz) is unhybridized.
Carbon will be sp2-hybridized if it is
directly bonded to three atoms in
25
Energy Level Diagram

Pz unhybrid.
PX PY PZ
Energy
after blending
SP2 SP2 SP2
sp2 hybrid
S S state of C.
G.S. Val. of Carbon E.S. Val. of Carbon
2s2 2p2

Orbital Blending Diagram

+ +
26
Sigma (δ) and Pi (π)
Bonds
Having seen the hybridization patterns
(sp3, sp2 and sp) of a single carbon, it
is of great interest to know that this
carbon can overlap with another
carbon to form either sigma (δ) and/or
pi (π) bond.

The hybrid orbital of adjacent carbon

atoms can overlap with one another or
with atomic orbital of other elements
such as sulphur, phosphorus, oxygen, 27
Sigma bond can be formed by
any of the following three
overlaps:
(i) Overlap of two hybrid
orbitals: These include sp3-
sp3, sp2-sp2, sp-sp, sp3-sp2,
sp -sp, sp -sp.
3 2

(ii)Overlap of a hybrid orbital

and s orbital e.g. sp3-s, sp2-s,
sp-s. 28
(i)
C C

sp3-sp3
Orbital Picture 3D-Structure

(ii)
C
H
H H
1s sp3-s
Orbital Picture 3D-Structure

(iii)
C

Cl Cl
3
sp -p
Orbital Picture 3D-Structure 29
two adjacent carbons are
unhybridized. It is a covalent bond
formed as a result of lateral overlap of
two unhybridized p-orbitals on
adjacent carbon atoms e.g. sp2-sp2 or
sp-sp overlaps result in π-bond
formation

Pi-bond 30
Sp-sp Overlap in Ethyne
(C2H2)
Overlap of sp-sp hybrid orbital of
two carbon atoms gives rise to a
triple bond (C Ξ C), which has 1δ +
2π-bonds.

The 2π-bonds are product of

lateral overlap of two unhybridized
p orbitals (i.e. 2py, 2pz) of one sp
carbon with that of other as seen
in ethyne (C H ). 31
Rotation about C Ξ C is the most
difficult. The bond energy of a C Ξ
C is also less than thrice the bond
energy of C-C, it has shortest bond
length of 1.20 Å becos of its
highest electron density.
Pi-bond

o
180
H C C H
H C C H H C C H
sigma sigma sigma
Orbital Picture 3D-Structure
Pi-bond
32
Example 2: Assuming the normal bond
angle at sp3, sp2 and sp hybridized C
atom, draw the graphical formula of
each of the following compounds in 3-
Dimensional representation.

(i) CH3CH2CΞCCH=CH2 (Hex-1-en-3-yne)

(ii) H2C=C(CH3)CH=CH2 (2-Methylbuta-1,3-
diene or isoprene)
(iii)CH3CH=CHCH2CΞCH (Hex-4-en-1-yne)
(iv) CH3CH=CHCH3 (Both cis- & trans-
but-2-ene)
(v) CH3CΞCCH=CH CΞCH (Hept-3-en-1,5- 33
Solution2: To solve this
problem, you need 3 things.
(i). Identification of the type
of hybridization for each
carbon.
(ii).Draw the graphical
formula showing the bond
angles and shape
(geometry). 34
(i) H C CH2 C
3 C CH CH2

3 3 sp 2 2
sp sp sp sp sp

H H b
e H a = b = 109.5o
a a c d
c = d = 180o
H C C C e
C C e = f = 120o
a a f
b
H H e C H
f
f

H 35