3.

E1 Elimination
Reaction Mechanisms 6

Anupam Gupta
Anupam Gupta
B.Tech & M.Tech - IIT Delhi

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E1 Elimination
Reaction Mechanisms 6

Anupam Gupta
 Reaction Mechanism

Nucleophilic substitution reaction:

Elimination reactions: Addition reactions:

● SN2 ● E1 ● Nucleophilic Addition to

● SN1 ● E2 carbonyls

● SNi ● E1cB ● Electrophilic Addition to

● SN2Ar ● Ei pi-bonds

● SN2Th
● Benzyne Mechanism

Electrophilic Substitution reactions

● EAS
 Elimination Reactions

β-elimination: When two groups are lost from adjacent atoms so that new π bond is
formed. This is also called 1-2 elimination.
 Elimination Reactions

α - elimination: When two groups are lost from the same carbon atom to give a
carbene. This is also called 1-1 elimination.
 Elimination Reactions

γ-elimination: It is also called 1-3 elimination, in this three membered ring is formed.
 Unimolecular Elimination (E1) Reaction

Proton and leaving group depart in two different step.

a. First step :
Slow step involves ionisation to form carbocation.
b. Second step :
Abstraction of proton.
 E1 Reaction of Alkyl halide: Dehydrohalogenation

Mechanism :
 Characteristics of E1 reaction

i. Unimolecular, two step process.

ii. First order reaction.
iii. Reaction intermediate is carbocation, so rearrangement is possible.
 E1 Reaction of Alkyl halide
Energetics :
The free energy diagram for the E1 reaction is similar to that for that SN1 reaction.
 E1 vs SN1
E1 and SN1 reactions are competing reactions
 E1 Reaction of Alkyl halide

Saytzeff (or Zaitsev) vs Hofmann product:

Correct statement for E1 Reaction is :
A. It is a two step process
B. Rearrangement is possible
C. Good leaving group favours
D. All of these
Which of the following will give three alkenes after dehydrohalogenation

A. B.

C. D.
Which one of the following compound undergoes E1 reaction most readily?

CH3
I
A. CH3 ー C ー CH2 ー CH3 B. CH3 ー CH2 ー CH2 ー Br
I
Br

CH3
I
C. CH3 ー CH2 ー CH2 ー I D. CH3 ー C ー CH2 ー CH3
I
I
 In the given reaction,

[X] as the major product among the elimination product is:

A. B. C. D.
 Major elimination product X.

X is:

A. B.

C. D.
 E1 Reaction of Alcohol

● Dehydration requires an acid catalyst to protonate the hydroxyl group of the alcohol
and convert it to a good leaving group.
E1 Reaction of Alcohol: Dehydration
 Elimination

● For E1 mechanism reagents are

i. H3PO4 / Δ
ii. H2SO4 / 1600
Mechanism :
 Factor affecting rate of E1 eliminations

Substrate - 30 > 20 > 10

Rate of reaction α stability of carbocation.
 Major Product

Major product is :

A. B. C. D.
In the reaction:

[X] will be:

A. B. C. D.
 Major product is

A. B. C. D.
 The product A is

A. B. C. D.
 In the given reaction [X] as major product

[X] will be :

A. B. C. D.
The relative rate of acid catalysed dehydration of following alcohols would be

A. III > I > IV > II

B. III > IV > I > II
C. I > III > IV > II
D. IV > III > I > II
Identify the major product formed in the following reaction

A. B.

C. D.
Which of the following does not representing the correct product

A.

B.

C.

D.
Intermediates for both the steps are respectively?

A. Carbocation & No intermediate

B. No intermediate & carbocation
C. Carbocation & carbanion
D. Carbocation & carbocation
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