Syllabus

• Introduction to organic chemistry. Structure properties.

• Alkanes.
• Alkenes I and II.
• Alkynes and dienes.
• Stereochemistry I and II.
• Alcohols and ethers.
• Alkyl halides.
• Cycloalkanes.

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 What is Organic Chemistry?
• Organic chemistry is one of the most
important branches in chemistry.
• It called organic because it was believed
that these compounds originated from
organisms.
• Organic compounds composite majority
of our bodies such as DNA, proteins, and
enzymes.
• The organic compounds can be studied
using the structure theory.

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 What is Structure theory?
• The structure theory is organizing how the
atoms are connected to make the bonds in
systematic way.
• It sets the rules and the facts that needs to be
followed.
• It shows how the order that the atoms are
connected and how.

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 Chemical Bonding
• It is the forces that keep the atoms together. K Br Na Cl
• There two main classes of bonds: ionic and
Ionic Bonds
covalent.
• The ionic bond is made by electron transfer
from one atom to another. H 3C H
• The covalent bond is made by sharing two
electrons. One from each atom. H 3C Br
• What is the rule for atoms to connect to each
other? H 3C OH
• By using atomic orbitals. Covalent Bonds

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 Atomic Orbitals Z Z Z Z
Y Y Y Y
• Atomic orbitals
are area in the
X X X X
space in which
the probability to p Orbital - py s Orbital
p Orbital - px p Orbital - pz
find the electron
is high. Z Z Z Z Z
Y Y Y Y Y
• Electrons
occupying a
certain orbitals X X X X X
according to their
d Orbitals d Orbitals d Orbitals d Orbitals d Orbitals
energy.

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 Electronic Configuration – Pauli Principle
1s
• Distribution of the electrons on the orbitals is H
based on certain rules.
He 2s 2p
• In 1925, An Austrian scientist called Wolfgang
Li
Pauli first and the fundamental rule.
Be
• The rule is named Pauli principle.
B
• It states that no two electrons have the same
C
state.
N
• Each orbital should occupy only two electrons.
O
• These two electrons should have opposite spin.
F
Ne
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 H
Formal Charge O O
O H H H
• It is the net charge on each atom H H
in the molecule.
• The formal charge is calculated H H
by subtracting the number of H N
N N
existing electrons from valence H H
H H H
electrons. H

C H
H H
N H H
N
C N
C H
H
H
C H
H H H H
H
H
H
H
C
H H H C C
O
H
C H H H H
H
C C O O O
H
H H H H H

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 Molecular Orbital MO H2 antibonding
molecular
orbital
Ψ1 - ψ2
• The theory shows that a new HUMO
orbital (molecular orbital MO)
is formed when the bond
formed.

Energy
H atomic H atomic
• The MO is less energy than orbital orbital
HOMO
the atomic orbitals. ψ1 H2 bonding
molecular ψ2
orbital
• The MO is hybrid between Ψ1 + ψ2
the atomic orbitals.
• It is the driving force for
making molecules. H atom H atom
• Both (H) atoms reach the
noble gas (He) electronic H2 Molecule
configuration.
σ bond
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 Bonding in Molecular Orbital MO
Antibonding
π* molecular
• The atomic orbitals from each atom orbital
approaches each other and start overlapping.
• The approaching continues and the
overlapping become more and more.

Energy
• Until the distance between the orbitals Atomic p
orbital
Atomic p
orbital
enable them to hybridize. Bonding π
• Head-to-head orbital overlapping gives σ molecular
orbital
bond.
• Side-to-side orbital overlapping gives π bond.

H2 Molecule 10
 Hybridization 2s 2p
C
• Let us take carbon atom as example.
2p
• It has two unpaired electrons. sp3
• So basically, it can form two bonds only.
• This not true in reality. 2s

• We all know that carbon atom form 4

2p
bonds.
sp2
• What is the possible explanation?
• A new hybridized orbital (sp3, sp2, and 2s
sp) is formed.
2p
• The hybridized orbital is less energy than
p orbital and more energy than s orbital. sp
2s
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Hybridization Exercise
O O

H 3C H 3C C C C C CH2
HO H H H

C CH

N O
C
H H2
C C
HC C C C N C O O
H H2
N

O CH3

H N

CH3

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 Hybrid Orbitals - sp
1s 2s 2p
• How the atoms make the covalent bonds with Be
each other?
• Let us take BeCl2 molecule as example for the
sp hybridization.
1s sp 2p
• Be does not have single electron to make a Be
covalent bond.
• One of electron in 2s orbital will be promoted
to one of the 2p orbitals to make a new hybrid 180˚
orbitals called sp.
• The angle between beryllium and chlorine is Cl Be Cl
180.
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 Hybrid Orbitals – sp2
1s 2s 2p
• Let us take BF3 molecule as example B
for the sp2 hybridization.
• B have only one single electron to
1s sp2 2p
make a three covalent bonds.
B
• One of electron in 2s orbital will be
promoted to one of the 2p orbitals to
make a new hybrid orbitals called sp2. 120˚
F F
• The angle between boron and fluorine
is 120. B

F
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 Hybrid Orbitals – sp3
1s 2s 2p
• Let us take CH4 molecule as example C
for the sp2 hybridization.
• C have only two single electrons to
1s sp3
make a four covalent bonds.
C
• One of electron in 2s orbital will be
promoted to one of the 2p orbitals to
make a new hybrid orbitals called sp2. H
• The angle between carbon and
109˚
hydrogen is 109.
C
H
H
H
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 Unshared Pairs of Electrons 1s sp3

• Let us take NH3 and H2O molecules N

as example for the molecules with
unshared electrons. 1s sp3
• NH3 have one unpaired electrons O
which will make the ammonia H

looks like a pyramid. H H H H

O N

• H2O have two unpaired electrons

which will make the water looks H
O
H H
N
H

like a bent. H

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 Polarity of Bonds
• Although the bonds are covalent, some
of them have some polarity.
• When one of the two atoms in the
bond have more electron density than F > O > Cl , N > Br > C, H
the other.
Highest
• The bond will be polar. electronegative
• The polarity of the bond is depending atom
on the electronegativity.
• The electronegativity is the tendency of
an atom to pull the electron density.

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 Polar Bonds
• Nonpolar bonds such as: H2, H H O O N N
O2, and N2.
• Polar bonds such as OH, CO, δ- δ+ δ- δ+ δ+ δ-
NH, CCl, HF, and CN. HO H H 2N H H 3C Cl

• δ- means it is partially δ- δ+ δ+ δ-
negative. F H H 3C NH2
• δ+ means it is partially
positive. F > O > Cl , N > Br > C, H
• As much difference in the 3.98 3.44 3.16 3.04 2.96 2.55 2.20
electronegativity between the Highest
two atoms as much the bond
is polar. electronegative
atom

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Polarity of the Molecules
• The molecule is considered polar if the dipole victors ( ) do not cancel
each other.
δ+ H
δ- δ-

δ- δ+ δ- δ-C O N
O C O δ+
H δ+ H H H H
H
δ+ δ+ δ+ δ+
H H
δ+ δ+

Nonpolar molecules Polar molecules

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Structure and Physical Properties
• Physical properties are very related to the
chemical structure.
• Melting point, boiling point, and solubility.
• These properties give us an idea about the
molecule structure and vice versa.
• These physical properties are very useful to
compound isolation, purification, and
characterization.

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Melting Point
• Melting point is one of the most fundamental physical properties.
• It measures the intermolecular forces strength by applying heat.
• In the melting point, a very well organized molecules in the crystal will be
transformed to much less organized liquid.
• Molecules have some attraction forces between them such as Van Der
Waals, dipole-dipole, hydrogen bonds, and ionic bond.
• As much as more attraction forces between the molecules in the crystal as
much as the melting point will increases.

Reference: Organic Chemistry by Janice Gorzynski Smith

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Boiling Point
• Boiling point is one of the most fundamental physical properties.
• It measures the intermolecular forces strength by applying heat.
• In the melting point, a less organized molecules in the liquid will be
transformed to much less organized gas.
• Molecules have some attraction forces between them such as Van Der
Waals, dipole-dipole, hydrogen bonds, and ionic bond.
• As much as more attraction forces between the molecules in the liquid as
much as the boiling point will increases.

Reference: Organic Chemistry by Janice Gorzynski Smith

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Solubility
• The golden rule “like dissolve like” polar solvents will dissolve polar
solutes and vice versa.

H
O
H H
H
O H H
O O
H
H H H
Na Cl O
H H
O O H H

H H H O O H

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Acids and Bases H2SO4 HCl
CH3COOH
Lowry-Bronsted. Bronsted Acids
• Acid is a material than can give a proton. NaOH
• Base is a material than can accept a proton. Mg(OH)2
For any given substance, as easily can give proton as stronger NH4OH
acid it will be and same rule will be applied to bases. Bronsted Bases

Lewis BF3 AlCl3

• Acid is a material that accept electron lone pair. Lewis Acids
• Base is a material that give electron lone pair.
Et3N Et2O
For any given substance, as easily can accept electron lone pair
as stronger acid it will be and same rule will be applied to bases. Lewis Bases

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Acids and Bases Strength
• As much stable is the
conjugated base as much the HCl OH HO H Cl
acid is stronger. Acid Base Conjugated Conjugated
• As much stable is the Acid Base
conjugated acid as much the
HA H 2O H 3O A
base is stronger.

• Ka reflect the strength of the weak acids. 𝐻𝐻3 𝑂𝑂+ 𝐴𝐴−

𝑘𝑘𝑎𝑎 =
• If the Ka have bigger value = strong acid. 𝐻𝐻𝐻𝐻
• If the pKa have smaller value = strong acid pKa = -log Ka
pKa < 1 very strong acid, pKa = 1 – 3 strong acids, pKa =
3 – 5 weak acids, pKa = 5 – 15 very weak acids, pKa >
15 very very weak acids.
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