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Nucleophilic Substitution Reaction

This document discusses the mechanisms of nucleophilic substitution (SN1 and SN2) reactions. It explains that in SN2 reactions, nucleophilic attack and bond breaking occur simultaneously in a single step. The rate depends on the concentrations of both reactants, making it second order. In contrast, SN1 reactions proceed through a two-step mechanism where a carbocation intermediate forms. The first step of leaving group departure is rate determining, making the overall rate first order dependent on the concentration of the alkyl halide. SN2 reactions result in inversion of configuration while SN1 reactions cause racemization due to the symmetrical carbocation intermediate. Steric effects influence the tendency of alkyl halides to undergo either mechanism.

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Pranjit Dey
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750 views18 pages

Nucleophilic Substitution Reaction

This document discusses the mechanisms of nucleophilic substitution (SN1 and SN2) reactions. It explains that in SN2 reactions, nucleophilic attack and bond breaking occur simultaneously in a single step. The rate depends on the concentrations of both reactants, making it second order. In contrast, SN1 reactions proceed through a two-step mechanism where a carbocation intermediate forms. The first step of leaving group departure is rate determining, making the overall rate first order dependent on the concentration of the alkyl halide. SN2 reactions result in inversion of configuration while SN1 reactions cause racemization due to the symmetrical carbocation intermediate. Steric effects influence the tendency of alkyl halides to undergo either mechanism.

Uploaded by

Pranjit Dey
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Nucleophilic substitution

reaction and sn1 sn2 reaction


mechanisms
By Pranjit Dey
BSc chemistry honors
Sem II
Alkyl Halides and Nucleophilic Substitution
The Polar Carbon-Halogen Bond
Alkyl Halides and Nucleophilic Substitution
The Polar Carbon-Halogen Bond
• The electronegative halogen atom in alkyl halides creates a
polar C—X bond, making the carbon atom electron
deficient. Electrostatic potential maps of our simple alkyl
halides illustrate this point.
Alkyl Halides and Nucleophilic Substitution
The Leaving Group
• In a nucleophilic substitution reaction of R—X, the C—X bond is
heterolytically cleaved, and the leaving group departs with the
electron pair in that bond, forming X:¯. The more stable the
leaving group X:¯, the better able it is to accept an electron pair.
Alkyl Halides and Nucleophilic Substitution
The Leaving Group
• There are periodic trends in leaving group ability:
Alkyl Halides and Nucleophilic Substitution

The Leaving Group


Alkyl Halides and Nucleophilic Substitution
Mechanisms for Nucleophilic Substitution
In a nucleophilic substitution:

But what is the order of bond making and bond breaking? In


theory, there are three possibilities.
[1] Bond making and bond breaking occur at the same time or (sn2)

In this scenario, the mechanism is comprised of one step. In such


a bimolecular reaction, the rate depends upon the concentration of
both reactants, that is, the rate equation is second order.
Alkyl Halides and Nucleophilic Substitution
Mechanisms for Nucleophilic Substitution
[2] Bond breaking occurs before bond making or (sn1)

In this scenario, the mechanism has two steps and a


carbocation is formed as an intermediate. Because the
first step is rate-determining, the rate depends on the
concentration of RX only; that is, the rate equation is first
order.
Alkyl Halides and Nucleophilic Substitution
Mechanisms for Nucleophilic Substitution
Consider reaction [1] below:

Kinetic data show that the rate of reaction [1] depends on


the concentration of both reactants, which suggests a
bimolecular reaction with a one-step mechanism. This is
an example of an SN2 (substitution nucleophilic
bimolecular) mechanism.
Alkyl Halides and Nucleophilic Substitution
Mechanisms for Nucleophilic Substitution
Consider reaction [2] below:

Kinetic data show that the rate of reaction [2] depends on


the concentration of only the alkyl halide. This suggests a
two-step mechanism in which the rate-determining step
involves the alkyl halide only. This is an example of an SN1
(substitution nucleophilic unimolecular) mechanism.
Alkyl Halides and Nucleophilic Substitution
Mechanisms of Nucleophilic Substitution
• All SN2 reactions proceed with backside attack of the
nucleophile, resulting in inversion of configuration at a
stereogenic center.
Alkyl Halides and Nucleophilic Substitution
Mechanisms of Nucleophilic Substitution

In sn2 reaction a total inversion of structure takes place as


the incoming nucleohile alays attacks from the back side
Alkyl Halides and Nucleophilic Substitution
Mechanisms of Nucleophilic Substitution

• Methyl and 10 alkyl halides undergo SN2 reactions with


ease.
• 20 Alkyl halides react more slowly.
• 30 Alkyl halides do not undergo SN2 reactions. This order
of reactivity can be explained by steric effects. Steric
hindrance caused by bulky R groups makes nucleophilic
attack from the backside more difficult, slowing the
reaction rate.
Alkyl Halides and Nucleophilic Substitution
Mechanisms for Nucleophilic Substitution
The mechanism of an SN1 reaction would be drawn as follows:
Note the curved arrow formalism that is used to show the flow
of electrons.

Key features of the SN1 mechanism are that it has two steps,
and carbocations are formed as reactive intermediates.
Alkyl Halides and Nucleophilic Substitution
Mechanisms for Nucleophilic Substitution
• Loss of the leaving group in Step [1] generates a planar
carbocation that is achiral. Attack of the nucleophile in Step [2]
can occur on either side to afford two products which are a pair
of enantiomers.
• Because there is no preference for nucleophilic attack from
either direction, an equal amount of the two enantiomers is
formed—a racemic mixture. We say that racemization has
occurred. But its not exactly racemic
Alkyl Halides and Nucleophilic Substitution
Mechanisms for Nucleophilic Substitution
Alkyl Halides and Nucleophilic Substitution
Mechanisms for Nucleophilic Substitution
• The rate of an SN1 reaction is affected by the type of alkyl halide
involved.

• This trend is exactly opposite to that observed in SN2 reactions.


Thank you

That’s all for my presentation and really like to


answer any of your questions related to my
presentation

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