Preliminary Idea of Reaction Mechanism

Preliminary Idea of Reaction
mechanism
BABITA ARYAL (BA)

Preliminary Idea of Reaction Mechanism
 The compounds which take part in chemical reactions are termed as

reactants and the compound which are formed as a result of chemical
reactions are known as products.
 The reactants are further classified as substrate and reagent. The reactant
undergoing attack is referred as substrate whereas the reactant working as
an attacking species is known as a reagent. The substrate and the reagent
interact to yield the product of a reaction under certain condition.
conditions
Substrate + Reagent Products
 The chemical (organic or inorganic) reactions are generally represented
using equations in which the reactant and products are written with an
arrow in between. The arrow points from the reactants towards the
products and the conditions of the experiment (catalyst, temperature, etc.)
are mentioned above and below the arrow.
 In the case of organic reactions to be carried out, there may be several

steps to be completed.
 The steps of organic reaction showing the breaking (fission) and the
making (formation) of bonds in the substrate leading to the formation of
products through transitory intermediates (unstable) often referred to as its
mechanism. Products
Substrate [intermediate]
Cleavage of covalent bond:
Reactions generally involve the breakage of preexisting bonds and formation of new bonds. Energy is
required for the cleavage of the bonds and energy is released during formation of new bonds. Covalent
bonds in organic compound may be broken by following two ways:
1) Homolytic bond fission or homolysis
2) Heterolytic bond fission or heterolysis
1. Homolytic bond fission or homolysis: When a covalent bond is symmetrically cleaved by equal
distribution of bonding electrons between two atoms, it is called homolysis or homolytic fission.
Generally, homolysis occurs between elements having equal or nearly equal electronegativity.
It takes place in the presence of sunlight or at high temperature and in gas phase.
Homolysis leads to the formation of free radicals.

heat or light
X + Y
X-Y or X : Y
free radical f ree radical
Homolysis
R-X or R:X R + X
dif f ued sunlight
Haloalkane f ree radicals
Free radicals:
The atom or group of atoms having unpaired electron or odd electron is

known as free radical. Because of the tendency of unpaired electron to
become paired free radicals are highly reactive intermediates. For eg:
Cl Chlorine free radical

CH3 methyl free radical
CH3CH2 ethyl free radical
C6H5 phenyl f ree radical
CH3COO acetate f ree radical
+ +
2. Heterolytic bond fission or heterolysis
 When a covalent bond is unsymmetrically cleaved by unequal

distribution of bonding electrons between two atoms, it is called
heterolysis or heterolytic fission. Generally, heterolysis occurs between
elements having different electronegativity.
 It takes place in the presence of polar solvent.
 Heterolysis leads to the formation of charged species (ions) called

cation and anion.
Q. What is hemolytic bond fission and heterolytic bond fission.

Carbocation
 If A has higher electronegativity then carbon atom, ‘A’ will take away
the bonding electron pair and it develops a +ve charge on carbon
atoms as cation and the resulting species is called carbocation.
 The organic species having only six electrons and positive charge on
C-atom are known as carbocations. They are highly unstable and
reactive.
CH3 methyl carbocation
CH3CH2 Ethyl cation
CH3CH2CH2 n-propyl cation
CH3-CH-CH3 iso-propyl cation

Carbanions :
 If A has lower electronegativity then carbon atom, ‘C’ will take away
the bonding electron pair and it develops a -ve charge on carbon
atoms as anion and the resulting species is called carbanion.
 The negative atom of carbanions has eight electrons in its shell. They
are highly unstable and reactive species.
CH3 :methyl carbanion
CH3CH2 Ethyl anion
CH3CH2CH2 n-propyl anion
CH3-CH-CH3 iso-propyl anion
Q. Define carbocation and carboanion.

Types of reagents:
2. Electrophiles or electrophilic reagents:
 A reagent or species which can accept an electron pair in the reaction is

called electrophile.
 Electrophiles are electron-loving species. So, electrophiles are positively

charged species or neutral species having electron deficient centre and
are called lewis acids.
 Electrophiles always attack on electron rich location in the molecule.

Electrophile is formed by heterolytic bond fission and it is represented by
E+.
C + E+ C E
Neutral electrophiles: BF3, AlCl3, FeCl3, SO3, CO2 etc

O
Positively charged electrophiles: H, NO2, SO3H, Cl, Br, R, CH3, H3O, R-C etc.
2. Nucleophiles or nucleophilic reagents: (nucleus loving)
 A reagent or species which can donate an electron pair in the reaction

is called nucleophiles.
 Nucleophiles (Nu¯) are nucleus loving or electron donating species. So

nucleophiles are negatively charged species or neutral species with
one pair of electrons and are called lewis bases.
 Nucleophiles always attack at the location where the electron density is

low. It is formed by heterolytic bond fission.
Neutral nucleophiles: NH3, H2O, R-O-H, R-O-R, R-NH2 , R2NH, R-S-H etc
Negatively charged nucleophiles: OH , H, CN, CH3 , R, Cl, Br, NO2, OR, etc.
3. Free radicals:
The atom or group of atoms having unpaired electron or odd electron is

known as free radical. Because of the tendency of unpaired electron to
become paired free radicals are highly reactive intermediates. For eg:
Cl Chlorine free radical

CH3 methyl free radical
CH3CH2 ethyl free radical
C6H5 phenyl f ree radical
CH3COO acetate f ree radical
+ +
Inductive effect
 Development of polarity in between the two covalently bonded atoms due to the difference
in electronegativity is called inductive effect. This effect is also called field effect.
 When the covalent bond is formed between two different electronegative atoms then the
bonding electrons are slightly migrated towards more electronegative atom. So, more
electronegative atoms bears partial negative charge and less electronegative atom from
which electrons are migrated bears partial positive charge. As a result polarity is produced in
the molecule.
 The inductive effect is shown by arrow ( ) pointing towards more electronegative element
or in the direction of electron displacement.
 For example:
Note: The continuous decline in the inductive effect with the increase in distance from the polar covalent bond is
shown by decrease in no. of arrows.
TYPES OF INDUCTIVE EFFECT
i) Positive Inductive effect (+I-effect)
Atoms or the group of atom which donate electrons towards the carbon
atom are said to have +I-effect. +I-effect are also called electron donating
or electron releasing groups. Such atoms or groups are more
electropositive than carbon atom.

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Preliminary Idea of Reaction

BABITA ARYAL (BA)

 The compounds which take part in chemical reactions are termed as

 In the case of organic reactions to be carried out, there may be several

1) Homolytic bond fission or homolysis

2) Heterolytic bond fission or heterolysis

Homolysis leads to the formation of free radicals.

The atom or group of atoms having unpaired electron or odd electron is

Cl Chlorine free radical

 When a covalent bond is unsymmetrically cleaved by unequal

 It takes place in the presence of polar solvent.

 Heterolysis leads to the formation of charged species (ions) called

Q. What is hemolytic bond fission and heterolytic bond fission.

CH3 methyl carbocation

CH3CH2 Ethyl cation

CH3CH2CH2 n-propyl cation

CH3-CH-CH3 iso-propyl cation

CH3CH2 Ethyl anion

CH3CH2CH2 n-propyl anion

CH3-CH-CH3 iso-propyl anion

Q. Define carbocation and carboanion.

 A reagent or species which can accept an electron pair in the reaction is

 Electrophiles are electron-loving species. So, electrophiles are positively

 Electrophiles always attack on electron rich location in the molecule.

Neutral electrophiles: BF3, AlCl3, FeCl3, SO3, CO2 etc

 A reagent or species which can donate an electron pair in the reaction

 Nucleophiles (Nu¯) are nucleus loving or electron donating species. So

 Nucleophiles always attack at the location where the electron density is

The atom or group of atoms having unpaired electron or odd electron is

Cl Chlorine free radical

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