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Chemical Reactions: Lecture by Kalpajyoti Dihingia Department of Chemistry DHSK College

This document summarizes a lecture on chemical reactions of haloalkanes. It discusses nucleophilic substitution reactions and elimination reactions of haloalkanes. For nucleophilic substitution, it describes how a nucleophile attacks the partially positive carbon atom of a haloalkane, replacing the halogen atom. It identifies two types of nucleophilic substitution mechanisms: SN2 and SN1. The SN2 reaction is bimolecular and concerted, while the SN1 reaction involves a unimolecular rate-limiting step forming a carbocation. Factors affecting the reactivity of each reaction are also summarized, such as the stability of carbocations determining the reactivity of SN1.

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44 views

Chemical Reactions: Lecture by Kalpajyoti Dihingia Department of Chemistry DHSK College

This document summarizes a lecture on chemical reactions of haloalkanes. It discusses nucleophilic substitution reactions and elimination reactions of haloalkanes. For nucleophilic substitution, it describes how a nucleophile attacks the partially positive carbon atom of a haloalkane, replacing the halogen atom. It identifies two types of nucleophilic substitution mechanisms: SN2 and SN1. The SN2 reaction is bimolecular and concerted, while the SN1 reaction involves a unimolecular rate-limiting step forming a carbocation. Factors affecting the reactivity of each reaction are also summarized, such as the stability of carbocations determining the reactivity of SN1.

Uploaded by

Kalpa Dihingia
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as ODP, PDF, TXT or read online on Scribd
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Chemical Reactions

Lecture by Kalpajyoti Dihingia


Department of Chemistry
DHSK college
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Reactions of Haloalkanes

●
Nucleophilic substitution reactions
●
Elimination reactions
●
Reactions with metal

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Nucleophilic substitution

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What is nucleophile ?
– Nucleophiles are electron rich species. They
attack at the part of the substrate which is
electron deficient.
– Nucleophile replaces already existing
nucleophile in a molecule called nucleophilic
substitution reaction.
– Haloalkanes are substituent in these reactions
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Nucleophilic substitution

●
Nucleophile attacts the partially positive C atom,
and the halogen atom as a leaving group
departs as halide ion.
●
This reaction is called nucleophilic substitution
reaction.
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Nucleophiles

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Species which contains negative charge/ lone
pair of electrons are nucleophiles.
●
Two types of nucleophiles

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Ambident nucleophile

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Table of SN reaction showing
reactants and products

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Two different mechanism

●
(1) SUBSTITUTION NUCLEOPHILIC
BIMOLECULAR (SN2)

●
(2) SUBSTITUTION NUCLEOPHILIC
UNIMOLECULAR (SN1)

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●
SN2 Reaction

●
This reaction follows 2nd order kinetics.
– Rate of the reaction depends upon concentration of both
the reactants.
●
Carbon-halide bond breaks, new bond is formed between C
and the attacking nucleophile starts forming.
●
This reaction takes place in one step.
●
Occurs through transition state in which both the reactants
are bonded partially to each other. 10 / 21
Important notes
●
In SN2 reaction the attack of the Nu¯ occurs from the back
side and the leaving group leaves from the front side.

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Walden inversion

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REACTIVITY OF SN2 REACTIONS

●
Tertiary halides are least reactive, because bulky
groups hinder approaching nucleophiles. The
order of reactivity followed is:
– Primary halide > Secondary Halide> Tertiary
halide

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Reactivity of SN2 Reaction

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SN1 reaction

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SN1 reactions

●
SN1 reactions are generally carried out in polar
protic solvents such as acid, water, alcohol,
acetic acid etc.
●
It follows first order kinetics.
●
In the following reaction, rate of the reaction
only depends on (CH3)3CBr

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SN1 Reaction

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REACTIVITY OF SN1 REACTION
●
REACTIVITY DEPENDS ON STABLITY OF
CARBOCATION.
●
GREATER THE STABLITY OF CARBOCATION,
GREATER WILL BE THE EASE OF FORMATION OF
ALKYL HALIDE AND FASTER WILL BE THE RATE OF
REACTION.

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ALLYLIC HALIDES & BENZYLIC HALIDES

●
Allylic and benzylic halides show high reactivity
towards SN1 reaction. The carbocation thus
formed gets stablised through resonance.

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References

●
NCERT book, Pradeep’s New course chemisty Vol
II, Class XII

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Thank You

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