Chapter 3

CHAPTER 3
AN OVERVIEW OF
COMMON MECHANISMS
LECTURER: PHAN THỊ HOÀNG ANH

I. KINDS OF ORGANIC REACTIONS
Based on the structure change of the reactant molecules
 Substitution reactions (S)
 Elimination reactions (E)
 Addition reactions (A)

2
 Rearrangement reactions
Rearrangement can accompany many of the reactions such as

substitution, addition, and elimination reactions.
3
Based on the way bond forming and breaking
Bond-breaking reaction → homolysis, heterolysis
Symmetrical bond-
breaking → radical
Unsymmetrical bond-
breaking → polar
Bond-forming reaction → homogenic, heterogenic
Symmetrical bond-
forming → radical
Unsymmetrical bond-
forming → polar 4
5
6
 Unimolecular reaction: one molecule is involved in the rate-determining step
 Bimolecular reaction: two molecules are involved in the rate-determining step
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8
Radical reactions
Chemical reactions that involve free-radicals
Radical substitution reaction
Radical addition reaction
9
Radical substitution of alkane
10
11
12
Polar reactions
 Polar reactions occur because of the electrical attraction between
positively polarized (Electrophile) and negatively polarized
(Nucleophile) centers on functional groups in molecules.
13
Nucleophile, electrophile
 Nucleophile (Greek - nucleus loving) : characterized by its ability to react
with a positive charge or partial positive charge
 Nucleophilic center: capable of donating a pair of electrons - may be
atoms possessing a localized lone pair, s bond, p bond.
 Nucleophiles can be either neutral or negatively charged
14
 Electrophile (Geek - electron loving): characterized by its ability to react
with a negative charge or partial negative charge.
 Electrophilic center: an electron-deficient atom with an empty
atomic orbital or a low-energy antibonding orbital, can form a bond by
accepting a pair of electrons from a nucleophile.
 Electrophiles can be either neutral or positively charged
15
 Electrons move from a Nucleophile to an Electrophile
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Formal charge
 Formal charge is the charge assigned to individual atoms in a Lewis
structure.
 Formal charges provide a method for keeping track of electrons, but
they may or may not correspond to real charges.
O: FC = 6 – (1 e bonding +
6e non bonding) = -1
20
CH4 C : FC = 4 – 4e bonding = 0
H: FC = 1 – 1e bonding = 0
NH4
N: FC = 5 – 4e bonding = +1
NH3-BH3
21
Common bonding patterns in organic compounds and ions
22
D.1.13. Determine formal charge in following structures
23
 L. 1.6
24
Curved arrow in polar reaction mechanisms
1. Curly arrow represents the actual movement of a pair of electrons
from an Nucleophile (Nu:)to an Electrophile (E).
25
2. Charge is conserved in each step of a reaction
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27
M1
3. The octet rule must be followed.
→ no second-row atom can be left with ten electrons (or four for
hydrogen).
→ If an electron pair moves to an atom that already has an octet (or
two for hydrogen), another electron pair must simultaneously move
from that atom to maintain the octet.
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29
M1
Mc.6.22. Add curved arrows to the following polar reactions to indicate the
flow of electrons in each:
30
Mc.6.23. Follow the flow of electrons indicated by the curved arrows in each of the
following polar reactions, and predict the products that result:
31
Mc. 6.39. Identify the bonds broken and formed in each step of the reaction, and
draw curved arrows to represent the flow of electrons in each step
32
Mc.6.41. Predict the product(s) of each of the following biological reactions by
interpreting the flow of electrons as indicated by the curved arrows
33
SOME COMMON REACTION MECHANISMS
Nucleophilic Substitution SN
Substitution Electrophilic Substitution SE
Radical Substitution SR
Electrophilic addition AE
Addition
Nucleophilic addition AN
Elimination 34
Nuclephilic substitution SN
 The characteristic reaction of alkyl halides
35
Electrophilic substitution SE
 The characteristic reaction of aromatic compounds
36
Radical substitution SR
 The characteristic reaction of alkanes
37
Electrophilic addition AE
 The characteristic reaction of unsaturated hydrocarbons (alkenes,
alkynes, alkadienes)
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39
Nucleophilic addition AN
 The characteristic reaction of carbonyl compounds
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41
Elimination reactions (E)
 The characteristic reaction of alkyl halides to prepare alkenes
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LECTURER: PHAN THỊ HOÀNG ANH

 Substitution reactions (S)

 Elimination reactions (E)

 Addition reactions (A)

Rearrangement can accompany many of the reactions such as

Bond-forming reaction → homogenic, heterogenic

 Bimolecular reaction: two molecules are involved in the rate-determining step

Radical substitution reaction

Radical addition reaction

Substitution Electrophilic Substitution SE

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