Chemical Reactions

Lecture by Kalpajyoti Dihingia

Department of Chemistry
DHSK college
1 / 21
Reactions of Haloalkanes

●
Nucleophilic substitution reactions
●
Elimination reactions
●
Reactions with metal

2 / 21
Nucleophilic substitution

●
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

3 / 21
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.
4 / 21
Nucleophiles

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

5 / 21
Ambident nucleophile

6 / 21
7 / 21
Table of SN reaction showing
reactants and products

8 / 21
Two different mechanism

●
(1) SUBSTITUTION NUCLEOPHILIC
BIMOLECULAR (SN2)

●
(2) SUBSTITUTION NUCLEOPHILIC
UNIMOLECULAR (SN1)

9 / 21
●
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.

11 / 21
Walden inversion

12 / 21
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

13 / 21
Reactivity of SN2 Reaction

14 / 21
SN1 reaction

15 / 21
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

16 / 21
SN1 Reaction

17 / 21
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.

18 / 21
ALLYLIC HALIDES & BENZYLIC
HALIDES

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

19 / 21
References

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

20 / 21
Thank You

21 / 21