Organic Reactions With Mechanism

Organic Reactions with
their mechanism
By
M.Fazal-ur-Rehman
BS (Hons) Chemistry
UE Lahore, Vehari Campus
Special Thanks to
Dr. Muhammad Atif

HoD Chemistry
(AP-Chemistry, UE Vehari Campus)
Organic Reactions and their mechanism by: M.Fazal-ur-Rehman UE Lahore, Vehari Campus
Organic Reactions
Generally, There are four types of organic reactions mentioned as;
• Addition
• Substitution
• Elimination
• Rearrangement
Nucleophilic Substitution Reaction

• A reaction, in which one nucleophile (Nu:) replaces the another nucleophile (Leaving Group)
bonded to electrophilic Carbon within Alkyl Halide; R-X, is called Nucleophilic Substitution
Reaction.
• It is denoted by “SN”; S-for Substitution , N-for Nucleophilic.
There are two types of Nucleophilic substitution reactions.
• SN1-Reaction
• SN2-Reaction
SN2-Reaction
• SN2- stands for Bi-molecular reaction. These are one step reactions, in which, the nucleophile attacks the
electrophilic Carbon directly. As the nucleophile comes in, the Carbon atom begins to acquire more than eight
electrons, so the bond to the leaving group breaks simultaneously. In the Transition State, the Carbon atom is
partially bound to both the nucleophile and the leaving group, forming an intermediate. The nucleophile
continues to come in and the leaving group continues to leave, until finally the product has been obtained.
R-X + Nu:  {Nu---R---X}  Nu-R + X- ………Rate Determining step
• The first step, which involved the Alkyl Halide and nucleophile, is rate determining step. So, rate is expressed
as;
Rate = k{Alkyl Halide}{Nucleophile}
• In these reactions, the inversion of configuration at chiral carbon in product is done, called Walden-inversion.
• These reactions are stereospecific because the reactant and products has no choice of pathway and are
stereospecific in nature.
• These reactions are concerted because the bond breakage of Leaving Group and bond formation of attacking
nucleophile with Alkyl Group, take place simultaneously.
SN1-Reaction
• SN1-stands for Uni-molecular Reaction. These are two step reactions, in which the partial breakage of bond present in
Alkyl Halide; R-X takes place and Cation and anion are formed. Simply say, Carbocation formation take place in first
step. Means, these reactions involve carbocation intermediates.
Step-I R-X  R+ + X- ………..Rate Determining Step
After formation of Carbocation, the nucleophile attacks on that carbocation in second step and forms the bond with it at
electrophilic carbon.
Step-II R+ + Nu-  R-Nu
These reactions depend on the concentration of Alkyl Halide. In these reactions, the first step is rate determining step in
which the Alkyl group is involved. So rate is written as;
Rate = k{Alkyl Halide}
• In these reactions, the bond breakage and bond formation not take place simultaneously, so these reactions are non-
concerted reactions.
• These reactions are non-stereospecific because the reactants and products are not stereospecific. The product is
actually racemic mixture in which retention and inversion of configuration of bonds are equal. In the second step, the
nucleophile rapidly attacks the free carbocation giving the product. The nucleophile can attack the carbocation from
either sides of the plane giving racemized product (with inversion and retention configuration).
If the leaving group departing from the substrate exists in the form of ion pair with the carbocation, partial recemization
occurs.
By: M.Fazal-ur-Rehman UE Lahore, Vehari Campus
SN1 v/s SN2-Reactions
Elimination Reactions
• In these reactions, two atoms are eliminated from two adjacent carbon atoms of substrate to form a multiple bond.
We also can say, the reactions in which the saturated Hydrocarbons are converted into unsaturated Hydrocarbons
with removal of two species from reactants; substrate, are called elimination reactions.
• As we said, two atoms are eliminated from adjacent carbon atoms, it means one atom is eliminated from α-carbon
while other atom is eliminated from β-carbon. Two bonds break in these reactions; the bond of C-X (at α-carbon) is
broken as well as the bond of C-H (at β-carbon).
• To proceed this, the β-Hydrogen (Hydrogen atoms attached to β-Carbon are called β-Hydrogen) must be available.
• If β-hydrogen is eliminated as proton, the elimination reaction is called β-elimination, a characteristic elimination
reaction.
• When the two atoms or groups are lost from one and the same atom of the substrate in an elimination reaction, the
reaction is said to be α-elimination reaction, which usually gives rise to a carbene, a reactive intermediate.
There are two types of elimination reactions mentioned as;
• E1-Reactions
• E2-Reactions
E2-Reactions
• These are bimolecular elimination reactions, similar to SN2- Reactions. In E2-Reactions, a base (B–)attacks a
Hydrogen atom bound to β-Carbon next to the electrophilic (α) Carbon. (B– here is the base, not boron. The
base might or might not be charged.) As the base forms its bond to H, the electrons in the C–H bond must leave
H and find somewhere else to go. They move to form a π bond to the electrophilic C next door. The electrophilic
C next door, though, has an octet, so at the same time as the π bond forms, the C–X bond must break. In the end,
the base has been protonated, X– has left, and an alkene has been formed.
• In these reactions, the base and nucleophile are involved in rate determining step. So, the rate of reaction is
given as;
Rate = k{Alkyl Halide}{Base}
E1-Reactions
• These are unimolecular, elimination reactions, similar to SN1-Reactions. These are two step reactions. In first step,
the leaving group leaves first to generate a carbocationic intermediate. Then , in second step, this intermediate then
undergoes a fragmentation (one of the three fundamental reactions of carbocation) to give an alkene and H+.
• Sometimes a base such as the departed leaving group is shown providing a new bond to H+ at the same time that
the C–H bond fragments, but sometimes no base is shown.
• In E1 reaction the rate of reaction only depends on the concentration of the substrate
Rate = k [substrate]

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Organic Reactions with

Dr. Muhammad Atif

Nucleophilic Substitution Reaction

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