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Organic Reaction Mechanisms IV: Elimination
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Dehydration of alcohols and dehydrohalogenation
JEE Main level
Single correct option
Difficulty 2 of 3
o4197
The order of ease of dehydrohalogenation by alcoholic
KOH
for ethyl bromide, isopropyl bromide and tert-butyl bromide is:
A
ethyl bromide
>
isopropyl bromide
>
tert-butyl bromide
B
isopropyl bromide
>
tert-butyl bromide
>
ethyl bromide
C
all three react at the same rate
D
tert-butyl bromide
>
isopropyl bromide
>
ethyl bromide
Answer: D
More alkyl substituents give more beta-hydrogens (statistical factor) and a more substituted, more stable alkene in the transition state. Therefore the
3
∘
halide eliminates faster than the
2
∘
, which eliminates faster than the
1
∘
.
Practice Organic Reaction Mechanisms IV: Elimination
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