Understanding The Elimination Reaction
Understanding The Elimination Reaction
Understanding The Elimination Reaction
•
•
•
•
•
•
•
•
•
•
•
•
Neighbouring group
participation by
Cyclopropyl methyl substrates
solvolyse with abnormally high rates.
Species having
lone pair
The products often include not
Aromatic rings as only disarranged cyclopropyl-
neighbouring groups methyl, but also cyclobutyl
and homoallylic compounds.
~ 47% ~ 5%
NaOH,
H2O
AcOH
AcOH
SOCl2
Ether
A PCl5
B C6H5-CH2-SNa
Δ
C SOCl2
D HI
Δ
A B
C D
A C
B D
Reaction of t-BuBr
slow
with dil. NaOH
t-Butyl
bromide fast or
t-butanol
Reaction of t-BuBr
with conc. NaOH
+ + +
t-Butyl Isobutene
bromide (2-Methylpropene)
The reaction stops being a substitution
and an alkene is formed instead.
General reaction
Alkene
E1
E2
𝛃-Elimination
reactions
E1cB
Ei
E1 describes an elimination reaction
ELIMINATION (E) in which RDS is unimolecular (1).
RDS
Carbocation
Step 1 Formation of carbocation
Slow
X + X‒
Carbocation
Step 2 Attack of base
+ +
TS (1)
TS (2)
Free energy (∆G)
Bˉ Xˉ
Bˉ
Slow
I + I‒
Carbocation
Step 2 Attack of base
+ +
CH3OH
Δ
CH3OH
(X)
Δ