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ORGCHEM LEC

STRUCTURAL EFFECTS
- Effect of the structure on STABILITY and
REACTIVITY of the organic compound

3. electron delocalization
(C-H hyperconjugation)

I. Resonance
- A molecules structure can have several forms that
differ only in the placement of electrons
- Electrons are shared between more than two
atoms (electrons are delocalized)
- Structural forms are called contributing structures
or resonance forms
TRUE STRUCTURE - Hybrid of all contributing or
resonance structures

How to show the movement of electrons?

:O:

:O:
C H

..
:O

.. :O:
N+

..
NH2

Allowed movement of electrons


Bond -> lone pair
B. Lone pair delocalization

Lone pair -> bond

Bond -> bond

* Only p bonds are broken or formed


Types of electron delocalization
1. electron delocalization
2. lone pair delocalization

C. Hyperconjugation
Electron delocalization involving sigma
bonds (C-C, C-H) and pi bonds.
More canonical structures lead to better
stability of the molecule
Double bonds can be:

I. Resonance
Molecules with resonance structures meet the ff
criteria:
Criterion 1: Have at least one pi bond.
Criterion 2: Have at least one of the following
a) A second, conjugated pi bond, or
b) An allylic or -atom with at least one lone
pair of electrons, or
c) An allylic atom with a vacant p-orbital.
Identifying structures with resonance
1. Does the molecule have at least one pi bond?
YES: a. number the 2 atoms of the pi bond 1 & 2
b. go to step 2.
NO: molecule does not have resonance.
2. Circle the atom(s) directly bonded to atom 1.
3. Circle the atom(s) directly bonded to atom 2.
4. Label the circled atoms 3, 4, 5, and 6.
5. Is atom 3, 4, 5 or 6 part of another pi bond?
YES: molecule has resonance
NO: Go to step 6.
6. Does atom 3, 4, 5 or 6 have at least one lone
pair of electrons or a single unpaired electron?
YES : the molecule has resonance
NO : Go to step 7.
7. Does atom 3, 4, 5 or 6 have a vacant p-orbital
(usually a carbocation)?
YES : molecule has resonance
NO : molecule has no resonance

II. INDUCTIVE EFFECT


Electronic effects of an atom or functional
group contributed through single bonds
Factors: electronegativity, position within the
structure
Inductive effect weakens with increasing
distance from the substituent
Inductive effect weakens with decreasing
electronegativity of the substituent
A substituent may WITHDRAW or
RELEASE electrons
ELECTRON-WITHDRAWING
SUBSTITUENT
-helps to offset negative charge
ELECTRON-RELEASING SUBSTITUENT
-helps to offset the positive charge

with excess positive charges


+

R N R

NH3

NO2

R
those with electronegative atoms

F
Cl
Br
groups exhibiting orbital electronegativity
NH2

C N

OH

OCH3

N N

those with easily polarizable valence electrons


I

CH3

CH2

Cl

CH3

CH2

CH3
+

H3C Cl

H3C N CH3
--

III. STERIC EFFECT


- Effect of atom or functional group on CROWDING
in the molecule

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