3.

E1cB & Ei Elimination

Reaction Mechanisms 8

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

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E1cB & Ei Elimination

Reaction Mechanisms 8

Anupam Gupta
E1cB : Unimolecular Elimination by Conjugate base intermediate
 E1cB : Conditions

(i) Substrate must be containing acidic hydrogens (stabilised by strong -l, -R)

(ii) Poor leaving groups (F, OH, OR, OPh, CN)

E1cB : Mechanism
 E1cB : Reversibility

Reversibility of the step can be observed by using Deuterated reagents

CH3 ー CH ー CH2 ー CH = O
l
OH
Reaction intermediate of E1cB reaction is
A. Carbocation
B. Carbanion
C. Benzyne
D. Free radical
 [NSEC - 2013]

The carbanion expels a leaving group LG to yield an alkene as shown

above by

A. E1 cB mechanism
B. E1 mechanism
C. E2 mechanism
D. Such a reaction does not take place
D - exchange is observed in
A. E1
B. E2
C. E1cB
D. None of these
 Major product is

A. B. C. D.
Major product of given reaction is

A. O2N ー CH = CH ー CH3 B. O2N ー CH2 ー CH = CH3

C. O2N ー CH = C ー CH3 D. CH2 = C ー CH3

l l
Cl NO2
The rate of elimination is fastest in

A. Ph ー CH2 ー CH3 ー F B. Ph ー C ー CH2ー CH2 ー F

ll
O

C. Ph ー O ー CH2 ーCH2ー F D. CH3 ー CH2ー CH2 ー F

 Ei Elimination Reaction Mechanism

● Ei mechanism (Elimination Internal/Intramolecular) Also known as a thermal syn

elimination or a pericyclic syn elimination

● Two vicinal substituents on an alkane framework leave simultaneously via a

cyclic transition state to form an alkene in a syn elimination.
 Pyrolytic Syn Elimination Ei (Elimination Intramolecular)

● Thermally activated and do not require additional reagents. Also called pyrolysis
reactions

● Substrates: Amine oxide, ester or xanthate undergo pyrolytic elimination of HX (in the
absence of any reagent), either in an inert solvent or, in some cases, in the gas phase.
 Pyrolytic Syn Elimination Ei (Elimination Intramolecular)

● In general these eliminations follow the rate law: Rate = K [substance]

 Ei Elimination Reaction Mechanism - Cope Elimination
When a tertiary amine oxide is heated at approximately 100oC, elimination reaction takes
place as follows:
Cope Elimination Regioselectivity
 Ei Elimination Reaction Mechanism - Ester Pyrolysis

● When subjected to temperatures above 400 °C, esters containing β-hydrogens can
eliminate a carboxylic acid through a 6-membered transition state, resulting in an
alkene.
Ei Elimination Reaction Mechanism - Xanthate Ester Pyrolysis
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