Chemistry Hydrocarbons MDCAT 2012
PMDC Verified Question 57 of 65
In the reaction of ethene with bromine the intermediate formed is
A
Cyclic bromonium ion
B
Primary carbocation
C
Bromine free radical
D
Carbanion
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option A: Cyclic bromonium ion
Concept:

Electrophilic addition of halogens to alkenes does not proceed through a standard open carbocation, but rather a stable three-membered cyclic intermediate.

Solution:

  • When ethene (\( \text{CH}_2=\text{CH}_2 \)) reacts with \( \text{Br}_2 \), the pi electrons attack the electrophilic bromine.


  • Instead of a full positive charge resting on one carbon, the bromine atom shares its lone pairs to bridge both carbons, forming a three-membered ring with a positive charge on bromine.


  • This intermediate is called the cyclic bromonium ion.


Why other options are incorrect:

  • A primary carbocation is highly unstable and would lead to rearrangement or unstereospecific addition; the cyclic intermediate explains the strict anti-addition of halogens.


  • Free radicals are involved in UV-catalyzed substitution, not cold electrophilic addition.


  • Carbanions are negatively charged species, impossible to form in electrophilic attack.

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