Introduction To Org Che

20 September, 2020
By : Zahra Kassem
Objectives
1. To identify different types of chemical bonds
2. To know how atomic orbitals combine to
form molecular orbitals.
3. To know why organic compounds have linear,
planar or tetrahedral structure.
4. To know the effect of hybridization on bond
length and acidity of the compounds.
5. To understand factors affecting electron
availability at a carbon atom
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PERIODIC TABLE
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Electronic configuration
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Types of chemical bonds

1- ionic Bond
11Na -e- 10 Na+ as Ne
17Cl +e- 18 Cl- as Ar
Na+ + Cl- NaCl
Electrostatic attraction between positive and negative ions
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2- Covalent Bond
Sharing of electrons between 2 atoms occur
through overlap of atomic orbitals to form
either σ or π bonds:
s spherical
p dumbbell-shape
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Types of overlap:
1) s and s overlap
(form σ bond)
2) s and p overlap
(overlap with only one lobe) (form σ bond)
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3) p and p overlap
a) head on overlap
b) Sidewise overlap
A π bond is not formed unless a σ bond is first formed
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3- Coordination Bond
( Semi-ionic Bond)
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4- Hydrogen Bond
Types of Hydrogen Bonds
a- Intermolecular hydrogen bond
Association hydrogen bond leads to increase in boiling point.

The increase in boiling point happens because the molecules
are getting larger with more electrons, and so van der Waals
dispersion forces become greater.
b- Intramolecular hydrogen bond
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valence
Valency
• It is number of unpaired electrons present in
the outermost shells
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Hybridization
• Is the idea that atomic orbitals fuse to form

newly hybridized orbitals, which in turn,
influences molecular geometry and bonding
properties.
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Methane CH4
Overlap of four sp3 orbitals of c atom with four
1s orbitals of four H atoms
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Methane CH4
• As seen in methane (CH4), carbon can form 4 bonds. The rationale

behind this phenomenon is hybridization. Supporting evidence
shows that 1 s and 3 p orbitals are being combined to form hybrid
orbitals, allowing polyatomic molecule to have 25% s character
and 75% p character. Thus, we call methane a sp3-hybridized
molecule.
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Ethylene
• The 2p orbital here is considered low enough energy to be
classified within the same energy level as the sp2 orbitals. The
figure below portrays the correct way to distribute electrons.
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Ethylene
• Notice how that lone electron in the 2p orbital is separate
from the electrons in the sp2 orbitals. This is what influence
ethylene's shape. The lone electron from each carbon will
remain in its respective p orbital and form a pi bond with the
other p orbital electron. Thus, ethylene is a planar molecule,
with orbitals spaced 120 degree angles apart.
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Acetylene
• 1 s orbital is being mixed with 1 p orbital.
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Acetylene
• the lone electrons in the 2p orbitals are not part of the sp

orbitals. Instead, each electron is in its respective p orbital,
and will bond with its respective p orbital of the other
carbon. This in itself will create a sigma bond and two pi
bonds, leading to the formation of a linear molecule!
Effect of hybridization
on
bond length and acidity
Electrons in S orbitals are strongly attached to

nucleus
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Effect of hybridization
on
bond length and acidity
Sp3 C Sp2c Sp C
Bond type
C-C C=C C ≡C
Example
CH3-CH3 CH2=CH2 CH ≡ CH
% S Character
25 33.3 50
Bond length
1.526 1.335 1.206 A O
Acidity
Non acidic Less acidic Most acidic
Bond Length and Bond Energy

• Bond Energy : Is the amount of energy
required to separate the bond pairs of atoms
to undefined distance : σ > π bonds.
• Triple>double>single
• Bond Length: It is the average distance
between centers of two adjacent atoms which
are bonded together ,bond length in single
bond is much longer than the double bond.
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Electronegativity
is the ability of an atom to attract bonded

electrons closer to itself
According to electronegativity:
F > O > N,Cl > Br > C,S > H
4.0 3.5 3.0 2.82 2.5 2.25
Factors Affecting Electron

Availability at an Atom
• 1 - Inductive effect
• 2 - Resonance
• 3 - Hyperconjugation
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1- Inductive effect
- I( out of Carbon ) +I ( to carbon)

electron withdrawing gp electron donating gp
e.g. NO₂,CN,SO₃H,CHO,COR e.g. Alkyl groups
F , Cl , Br , I
2- Resonance
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↑ number of canonical structures →↑ stability
Inductive effect Resonance
Occur only in saturated Occur in unsaturated and

systems conjugated systems
It is the tendency of an Delocalization of π es or

atom or group of atoms to lone pair in a planar
attract or release electrons system
(parallel p orbitals)
Transmission effect fades Continue as long as
by increasing distance conjugation extends
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Breaking of a covalent bond

A) homolytic fission
B) heterolytic fission
Breaking of a covalent bond

• Homolytic bond fission, is the breaking of a bond
that results in one electron going to each atom in the
bond. Homolytic cleavage is the source behind free
radicals--atoms with one electron in an orbital and
no charge (actual atoms--not ions).
• Heterolytic cleavage, which is more common, refers

to a bond breaking and one atom getting both
electrons while the other gets none.
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List of References
Essential Books (Text Books):
- Textbook of Organic Medicinal and Pharmaceutical Chemistry, Wilson and
Gisvold's, 12th Ed., International Edition, Philadelphia : Lippincott Williams
& Wilkins, 2011.
- Textbook of Organic Medicinal and Pharmaceutical Chemistry, Wilson and
Gisvold's, 11th Ed., Philadelphia : Lippincott Williams & Wilkins, 2004.
- Organic Chemistry ,T. W. Graham Solomons, Craig B. Fryhle, 9th Ed., N.Y.:
John Wiley & Sons, Inc., 2006.
- Organic Chemistry, T. W. Graham Solomons, Craig B. Fryhle, 8th Ed., N.Y.:
John Wiley & Sons, Inc., 2004.
- March's Advanced Organic Chemistry,: Reactions, Mechanisms, And
Structure, Michael B. Smith and Jerry March, 6th Ed., New Jersey : John
Wiley and Sons, Inc., 2007.
- Organic Chemistry, John McMurry, 7th Ed., Australia : Thomson
Brooks/Cole, 2008.
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20 September, 2020

Types of chemical bonds

17Cl +e- 18 Cl- as Ar

Na+ + Cl- NaCl

Electrostatic attraction between positive and negative ions

(overlap with only one lobe) (form σ bond)

A π bond is not formed unless a σ bond is first formed

Association hydrogen bond leads to increase in boiling point.

b- Intramolecular hydrogen bond

• Is the idea that atomic orbitals fuse to form

• As seen in methane (CH4), carbon can form 4 bonds. The rationale

• 1 s orbital is being mixed with 1 p orbital.

• the lone electrons in the 2p orbitals are not part of the sp

Electrons in S orbitals are strongly attached to

Bond Length and Bond Energy

is the ability of an atom to attract bonded

Factors Affecting Electron

- I( out of Carbon ) +I ( to carbon)

↑ number of canonical structures →↑ stability

Inductive effect Resonance

Occur only in saturated Occur in unsaturated and

It is the tendency of an Delocalization of π es or

Breaking of a covalent bond

Breaking of a covalent bond

• Heterolytic cleavage, which is more common, refers

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