Reactions, Mechanisms &
Kinetics
B.Tech F.Y SEM I
CHEMISTRY
Dr.Shabdashri Bhange
Introduction:-
Organic chemistry is the branch of Chemistry that involves the
scientific study of organic compounds (compounds that contain
covalently bonded carbon atoms).
This branch of chemistry primarily deals with the structure and
chemical composition of organic compounds, the physical and
chemical properties of organic compounds, and the chemical
reactions undergone by these compounds.
The reactions in organic chemistry occur between organic compounds.
Cleavage of Bonds:-
The reactions in organic chemistry occur through the breaking and
making of bonds. Bonds can cleave in either of two ways:
A) Homolytic cleavage
B) Heterolytic cleavage
A)Homolytic cleavage
If the covalent bonds between two elements break in such a way
that each of the elements gets its own electrons, it is
called homolytic cleavage. That is, each element gets an electron.
Homolytic cleavage results in the formation of free radicals.
In the above figure, we have used an arrow to show the movement
of electrons. Here, in this case, the arrow used is called the fish-
hook arrow, as it signifies that there is a movement of only one
electron.
B) Heterolytic cleavage
If the covalent bonds between two elements break
heterolytically, i.e., unequally, it results in the formation of charged
species. This type of bond breaking, where the electrons are
unevenly distributed, is called heterolytic cleavage.
As before, an arrow with double-barbs is used to show heterolytic
cleavage, which is the transfer of the electron pair specifically:
Sr. Homolytic bond fission Heterolytic bond fission
No
1 The symmetrical breaking of a The unsymmetrical breaking of a
covalent bond in which each covalent bond in which each departing
departing atom takes one electron atom takes both bonding electrons is
from bonding pair is called as called as heterolytic fission
homolytic fission
2. In this type of fission formation of In this type of fission formation of
free radicals containing unpaired charged species called as ions like
electrons are formed. carbocation and carbanion takes place
3 The covalent bond between two The covalent bond between two atoms
atoms of same element or two atoms of different element or two atoms
having nearly same electronegativity having nearly different electro
breakes in this manner negativity breakes in this manner
4. Generally reactions takes place at Generally reactions takes place in
high temperature or in presence of solutions.
UV light or peroxide
Reagents
Reagents are the chemicals that we add to bring about a specific
change to an organic molecule. Any general reaction in organic
chemistry can be written as follows:
Substrate + Reagent → Product
Where the substrate is an organic molecule to which we add the
reagent. Based on the ability to either donate or abstract
electrons, the reagents can be classified as follows:
A) Electrophiles
B) Nucleophiles
A) Electrophiles
An electrophile is an electron-deficient species that can accept a
pair of electrons
‘Electrophile’ means ‘electron/negative charge loving’ as
electrophiles are attracted to negatively charged species
Electrophilic refers to reactions that involve an electrophile.
Examples:-
B) Nucleophiles:
A nucleophile is an electron-rich species that can donate a pair
of electrons
‘Nucleophile’ means ‘nucleus/positive charge loving’ as
nucleophiles are attracted to positively charged species
Nucleophilic refers to reactions that involve a nucleophile
Examples:-
Types of Organic Reactions:
When organic substances are involved in a chemical reaction it is
referred to as an organic reaction.
The four major types of organic reactions are:
Substitution Reactions
Elimination Reactions
Addition Reactions
Radical Reactions
Oxidation-Reduction Reactions
Substitution Reactions:
A substitution reaction is defined as the direct replacement
(displacement or substitution) of an atom or group of atoms in an
organic molecule by another atom or group of atoms without
causing any changes to the remaining components of the
molecule.
The new atom or group of atoms that enter the molecule is
known as the substituent, and the product produced as a result of
the substitution is referred to as the substitution product. For
example,
Reaction Mechanism of Substitution Reactions
Two types of organic reactions and their mechanisms are:
•SN1 (Substitution, nucleophilic, unimolecular)
•SN2 (Substitution, nucleophilic, bimolecular)
SN1 (Substitution, nucleophilic, unimolecular)
The SN1 reaction is a type of nucleophilic substitution reaction in
which an electron-rich nucleophile displaces the halogen atom
bonded to the central carbon of an alkyl halide molecule. The halide
ion that is displaced from the carbon atom is called the leaving group.
SN1 reaction takes place at the site of a saturated carbon atom.
Some typical nucleophiles are halide (X–), hydroxy group (OH–),
alkoxy group (RO–), cyanide ion (CN–),
Kinetics of SN1 reaction:-
Rate of SN1 reaction depends upon the concentration of alkyl halide
and is independent of the concentration of nucleophile. Thus the
reaction follows first order kinetics.
Mechanism of SN1 reaction
Two-step reaction process:
Step 1:- Slow Step carbon-halogen bond breaks, resulting in a
positively charged carbon (carbocation) and Unimolecular and follows
first-order kinetics
Carbocation stability: 3º > 2º >> 1º
Step 2:- Fast step nucleophile attacks the carbocation, forming a
new bond
Rate of the reaction depends on the concentration of the substrate
(alkyl halide)
Polar protic solvent is used to enhance the reactivity
Mostly occurs in tertiary and secondary alkyl halide
SN1 reaction has racemization stereochemistry, i.e., both retention
and inversion products are formed
The order of reactivity of halides towards SN1 reaction is
I–>Br–>Cl–>F–. In other words, the C-I bond is easy to break than the
C-F bond, making the former susceptible to nucleophilic attack
Energy profile diagram of SN1 reaction
SN2 (Substitution, nucleophilic, bimolecular)
SN2 reaction is also known as bimolecular nucleophilic
substitution reaction. Such reactions are generally shown by
primary haloalkanes. For example, hydrolysis of ethyl bromide with
aq.KOH.
Kinetics of SN2 reaction:-
Rate of SN2 reaction depends upon the concentration of both
substrate (i.e. alkyl halide) and nucleophile. Thus the reaction
follows second order kinetics since both the reactants are present
in rate determining step.
Mechanism of SN2 reaction
The mechanism of SN2 reaction involves a single step. Therefore,
the breaking of carbon – halogen (C – X) bond and making of carbon
– nucleophile (C – OH) bond occurs simultaneously.
Carbocation stability: 1º> 2º > 3º
Energy profile diagram of SN2 reaction
Difference between SN1 and SN2 reaction
Synthesis of Drugs:-
1) Synthesis of Chalcone:-
2) Synthesis of Paracetamol:-
3) Synthesis of Asprin:-
