NS 8110
ORGANIC CHEMISTRY
LECTURE ONE
BSc. EDUCATION
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Organic Chemistry
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ORGANIC CHEMISTRY: INTRODUCTION
• To early 19th Century Chemists, organic chemistry
meant the study of compounds obtainable only
from living matter
• Thought to have “vital force” needed to make
these compounds
• Organic compounds are the primary constituents of
all living organisms.
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• 1828 Friederich Wöhler set out to synthesize
ammonium cyanate, NH4OCN as in the reaction:
AgOCN(s) + NH4Cl(aq) AgCl(s) + NH4+OCN-
O
NH4+OCN- heat H2N C NH2
ammonium cyanate urea, a urinary excretion
"inorganic" of mammals product
" organic"
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• Wöhler obtained a white crystalline solid
compound from the solution with the same
composition but had none of properties of
ammonium cyanate
• The compound was not ammonium cyanate but
urea
• Wöhler was excited and reported to Berzelius:
“I must tell you that I can make urea without
the use of kidneys, either man or dog.
Ammonium cyanate is urea!!!”
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Organic Chemistry: now includes the study of
carbon compounds which are found not only
in living things but also those synthesized in
the laboratory.
Organic chemistry is the study of carbon & carbon
compounds except CO, CO2, CO32-, and carbides
Position of X can be occupied by
another carbon or any other
element
Carbon is able to form 4 covalent bonds (4 valence
electrons) with other carbon or other elements.
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What makes carbon so special?
• It has a “central” role in all living organisms.
• It has 4 valence electrons.
• It makes 4 covalent bonds.
• It can bond with any element, but really loves to
bond with other carbon atoms and make long
chains
Carbon atoms bind strongly to each
other and form very large molecules
which are built around this carbon
'backbone'.
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Some organic chemicals
DNA Medicines
•Active Pharmaceutical Ingredients
•Excipients
Fuels
Materials
4/17/2026 Essential oils Pigments8
Characteristics of Organic Compounds
✓ They are nonpolar compounds – they do not dissolve
in polar solvents like
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Characteristics of Organic Compounds
✓ They have low melting points – due to weak
intermolecular forces.
✓ They react slower than ionic compounds – due to
strong covalent bonds between atoms.
✓ Unable to make salt due to covalence nature of
carbon bonds.
✓ Poor conductors of heat and electricity
✓ Highly inflammable due to ability to undergo
combustion
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CHEMICAL BONDS
Types of bonds:
– Ionic Bond (Electrovalent): Results when two atoms of
different electronegativities react by electron transfer.
– Covalent Bond: bond that results from sharing of
electrons by atoms to obtain octet structure-
configuration of noble gases (each bonding atom donate
electron)
– Dative Bond: bond that result when an atom donates its
unpaired electrons to another atom (Only one of the
bonding atoms donate electron pair)
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OCTET RULE
Fam i l y # C ov al en t Bon d s*
→
H al ogen s
X 1 bond often
F, B r, C l , I
C alcogen s
O, S
O → 2 bond often
N i trogen
N,P
N → 3 bond often
C arb on
C → 4 bond always
C , Si
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COVALENT BONDS
• Occurs when two atoms of the same or similar
electronegativities react whereby a complete
transfer of electrons does not occur and form
noble gas configuration by sharing of electrons
eg:
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ATOMIC STRUCTURE OF CARBON
Carbon has six electrons, which occupy different atomic
orbitals of different energies
Electronic configuration of Carbon C 1s2 2s2 2p2
Two unpaired electrons
So one could think that carbon is able to
make only two covalent bonds
But carbon always make FOUR bonds
because of hybridization of outer shell
orbitals
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HYBRIDIZATION AND TYPES OF BOND
• The mixing of s and p orbitals to form a new hybrid
orbitals that allow carbon to form FOUR bonds which
are always observed in reality
• There are three different ways of how the s and p
orbitals are mixed, resulting in the three classes
(alkane, alkene and alkyne) of the aliphatic
hydrocarbons
• Outer orbitals can undergo three different
hybridizations; sp3 forming C-C single bond (alkane)
sp2 (for alkene) and sp forming triple bonds (alkynes)
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sp3 Hybridization
• The 2s orbital is mixed with all three 2p orbitals
• The number of hybrid orbitals equals the number of
original orbitals, 4
• The energies of these hybrid sp3 orbitals is greater
than the original 2s orbital, but smaller than the
original p orbitals
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The four half-filled sp3 orbitals can form four bonds and
this explains why Carbon is tetrahedral in saturated organic
molecules such as alkane
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sp3 Hybridization
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sp2 Hybridization
• The 2s orbital is mixed with only two of the 2p orbitals to
form 3 hybrid orbitals i.e sp2 hybrid orbitals
• The third p orbital remains unaffected and is used for
one π-bond formation
• The energies of these hybrid sp2 orbitals is greater than
the original 2s orbital, but smaller than the p orbitals
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Views of Ethylene, C2H4
1- s bond and 1-p bond
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sp Hybridization
• The 2s orbital is mixed with only one of the 2p orbitals
and form 2 hybrid orbitals i.e sp hybrid orbitlas
• The other two p orbital remains unaffected and are used
for two π-bond formation
• The energies of these hybrid sp orbitals is greater than
the original 2s orbital, but smaller than the p orbitals
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Acetylene, C2H2 → CH≡CH
1s bond and
2 perpendicular π bonds
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FUNCTIONAL GROUPS
• Organic chemistry is a vast subject so it is easier to
split it into small sections for study.
• This is done by studying compounds which behave
in a similar way because they have a particular
atom, or group of atoms “FUNCTIONAL GROUP” in
their structure.
• Functional groups can consist of one atom, a group
of atoms or multiple bonds between carbon atoms.
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• Each functional group has its own distinctive
properties
• The properties of a compound are governed by the
functional group(s) in it.
H H H H H H H H H H
H C C C C C NH2 H C C C C C OH
H H H H H H H H H H
Carbon Functional Carbon Functional
skeleton Group = AMINE skeleton Group = ALCOHOL
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COMMON FUNCTIONAL GROUPS
GROUP ENDING GENERAL FORMULA EXAMPLE
ALKANE - ane RH C2H6 ethane
ALKENE - ene C2H4 ethene
ALKYNE - yne C2H2 ethyne
HALOALKANE halo - RX C2H5Cl chloroethane
ALCOHOL - ol ROH C2H5OH ethanol
ALDEHYDE -al RCHO CH3CHO ethanal
KETONE - one RCOR CH3COCH3 propanone
CARBOXYLIC ACID - oic acid RCOOH CH3COOH ethanoic acid
ACYL CHLORIDE - oyl chloride RCOCl CH3COCl ethanoyl chloride
AMIDE - amide RCONH2 CH3CONH2 ethanamide
ESTER - yl - oate RCOOR CH3COOCH3 methyl ethanoate
NITRILE - nitrile RCN CH3CN ethanenitrile
AMINE - amine RNH2 CH3NH2 methylamine
NITRO nitro- RNO2 CH3NO2 nitromethane
SULPHONIC ACID - sulphonic acid RSO3H C6H5SO3H benzene sulphonic acid
ETHER - oxy - ane ROR C2H5OC2H5 ethoxyethane
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COMMON FUNCTIONAL GROUPS
ALKANE CARBOXYLIC ACID
ALKENE
ALKYNE
ESTER
HALOALKANE
ACYL CHLORIDE
AMINE
NITRILE
AMIDE
ALCOHOL
ETHER
NITRO
ALDEHYDE
SULPHONIC ACID
KETONE
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CLASSIFICATION OF ORGANIC COMPOUNDS
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1. Acyclic or Aliphatic /open chain
compounds
Consist of straight or branched chain compounds, for
example: CH3CH3 CH3CH2CH3 CH3CH=CH2
CH3
H
C
HO C
O CH3
O
Ethanal Ethanoic acid
2. Alicyclic or closed chain or ring compounds
O
cyclopropane cyclobutane Tetrahydrofuran
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Structural Formulas
A 2D model shows bonding patterns and shapes of
molecules
Carbon is found in the center H
H C H
The short line/bonds (–) represents a
pair of electrons. H
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Drawing the structures
H
1. Methane: CH4
H C H
2. Chloroform: CHCl3 H
H
Cl C Cl
3. Ethane: C2 H6
Cl H H
Remember : Carbon has H C C H
4 bonding sites.
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Depicting cycloalkanes
H H
H H
H C C H
C
H C C H H C C H
cyclopropane cyclobutane H H
H H
H H
H H
H H C
H C H H C C H
C C
H H H C C
C H
C
H C H cyclohexane H
H H
H
cyclopentane H H
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Types of organic reactants
I. A nucleophile is an electron-rich atom that can
form a bond by donating a pair of electrons to a
electron poor specie. It is a “nucleus-loving.”
Nucleophiles include:
➢ Species with Net negative charge (-)
➢ Example: RO‒ , ‒NH2, R2N‒, RO‒, RS‒
➢ Species with π bond electrons
➢ Species with Lone pair(s) of electrons
Example: H2O, NH3, RNH2, R2NH, ROH
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II. Electrophile
➢ An electrophile is an electron poor atom that can
form a bond by accepting a pair of electrons from a
nucleophile.
➢ An electrophile is an “electron-loving.”
Electrophiles include:
➢ Species with net positive charge (+)
For example, H+, CH3CH2+, Cl+, CH3+, NO2+
➢ Species with empty orbital in their electronic
structure (Lewis acid) such as AlCl3, FeCl3
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III. A Free radical
➢ A free radical is an atom or group of atoms with
unpaired electron in their electronic structure; so
they share the unpaired electron during organic
reactions
➢ Unpaired electron is represented by a single dot, for
example Cl· and CH3·
➢ Free radicals are formed during hemolytic bond
cleavage
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Bond formation and bond cleavage
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CURVED ARROW NOTATION
• The curved arrow notation shows the movement
of electrons (electron flow)
• Electrons from the “source” to the “sink”
e- pair Single e-
Double-headed arrow Fishhook arrow
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REACTION MECHANISM
• Reaction Mechanism: a step by step account of all
the electrons and bond changes in a chemical
reaction.
• The species that donated lone pair electrons
become positive, and this positive charge can’t be
neutralized by adding more electrons but rather
by breaking one of its old bonds which must be
different from newly formed bond.
• If electrons are from double bond, arrow must
pass near the atom donating π bond electrons.
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Electron “source” Electron “sink” Product
Non bonding pair to adjacent bond
(vertex-to-edge transfer)
Bonding pair to an adjacent atom (edge-
to-vertex transfer)
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Show the reaction mechanism for the following
reactions:
• Ethene reacts with HCl
• Ethene reacts with water in presence of acid.
• Methane reacts with chlorine gas under UV light.
• Ethene reacts with N-methylethanamine (2°
amine) in presence of acid.
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EMPIRICAL FORMULA
• Empirical formula is the simplest formula showing the
relative numbers of the different kinds of atoms in a
molecule, example in 100 g of methane, there are 74.9 g
of carbon and 24.9 g of hydrogen
• Dividing each quantity by the proper atomic weight, gives
the number of moles of each element:
C: 74.9/12.01 = 6.24 moles
H: 24.6/1.008 = 24.7 moles
Therefore, we have: C6.24H24.7
Dividing by the smallest number:
C: 6.24/6.24 = 1, H 24.7/6.24 = 3.96 (approx. 4)
Therefore, the empirical formula of methane if CH4
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MOLECULAR FORMULA
• Molecular formula: is the formula that shows
the actual number of each kind of atom in a
molecule
• Gives information about what kinds of atoms
are there and how many each of them make up
a molecule
• To determine the molecular formula of a
molecule we need to have the molecular
weight, which is determined by mass
spectrometry
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To establish the molecular formula of a
compound, the following must be carried out:
– A qualitative elemental analysis: to find out what kinds
of atoms are present in the molecule
– A quantitative elemental analysis: to find out the
relative numbers of the different atom, i.e. to determine
the empirical formula
– A molecular formula determination: can be obtained
from empirical formula if molecular weight is known
– Molecular weight: Can be obtained from vapor density,
colligative properties and/ or Mass spectrometry
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• A qualitative elemental analysis:
– Presence of carbon or hydrogen in a compound is
detected by combustion:
• A quantitative elemental analysis: C, H
– Quantitative combustion is used
– Example: A sample of methane weighing 9.67 mg
produced 25.53 mg of CO2 and 21.56 mg of H2O,
calculate the empirical formula.
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Calculation:
• Only the fraction C/CO2 = 12.01/44.01 of the
carbon dioxide is carbon and only the fraction
2H/H2O = 2.016/18.02 of the water is hydrogen
Therefore:
Weight of C = 25.53 x 12.01/44.01 = 7.24 mg
Weight of H = 21.56 x 2.016/18.02 = 2.41 mg
% composition:
%C = (7.24/9.67) x 100 = 74.9
%H = (2.41/9.67) x 100 = 24.9
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Practice Exercise
1. Combustion of 6.51 mg of a compound gave
20.47 mg of carbon dioxide and 8.36 mg of water.
The molecular weight was found to be 84.
Calculate:
a) percentage composition of each atom
b) empirical formula
c) molecular formula of the compound
2. A liquid of molecular weight 60 was found to
contain 40.0% carbon and 6.7% hydrogen.
What is the molecular formula of the compound?
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3. 10 cm3 of a hydrocarbon CaHb were exploded with
excess oxygen. A contraction of 25 cm3 occurred. On
treating the product with sodium hydroxide a further
contraction of 40 cm3 occurred. Deduce the values of a
and b in the formula of hydrocarbon. All measurements
of gas volumes are at s.t.p
4. When 20 cm3 of a gaseous hydrocarbon were sparked
with 150cm3 of oxygen and the residual gases cooled to
rtp, a contraction of 60 cm3 occurred. A further
contraction of 80 cm3 took place when the residual gases
were subjected to aq NaOH. All the volumes were
measured at 25 degrees. (i) Determine the formula of the
hydrocarbon. (ii) Excess volume of oxygen.
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5. 10 cm3 of a hydrocarbon C4H8 were exploded with
excess oxygen. A contraction of a occurred. On treating
the product with sodium hydroxide a further
contraction of b occurred. What are the volumes, a and
b? All measurements of gas volumes are at s.t.p
6. 10 cm3 of gaseous hydrocarbon Q required 45 cm3 of
oxygen for complete combustion. Q reacts with one
mole of bromine gas to form a brominated of molecular
mass 200 g/mol which contain 79.2% bromine.
Determine the molecular formula of Q and two
possible structure of Q.
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