Electrophilic addition of bromine

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SUMMARY

The electrophilic addition of bromine to alkenes involves a bromine molecule approaching the pi electron cloud of the C=C bond, leading to the formation of a pi complex. The bromide ion subsequently attacks the pi complex nucleophilically from the opposite side of the first bromine, resulting in a trans product. This trans attack is favored due to steric effects, which influence the electron density during the reaction. Understanding these mechanisms is crucial for predicting the stereochemistry of the dibromo product.

PREREQUISITES
  • Understanding of electrophilic addition reactions
  • Familiarity with alkene structures and reactivity
  • Knowledge of steric effects in chemical reactions
  • Basic grasp of nucleophiles and electrophiles
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  • Study the mechanism of electrophilic addition reactions in detail
  • Explore the concept of steric effects in organic chemistry
  • Learn about the stereochemistry of addition reactions
  • Investigate other electrophilic addition reactions involving different halogens
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Chemistry students, organic chemists, and anyone studying reaction mechanisms in organic synthesis will benefit from this discussion.

Clari
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Hi! I am stuck in revising the electrophilic addition of bromine across the alkene molecule... There are two sentences which really confuse me, I hope you can help me.

When a bromine molecule approaches the pi electron cloud of the C=C bond...the bromide ion then attacks the pi complex nucleophilically from a side opposite to the first bromine. This becomes known as a trans attack and the result is a dibromo product.

My question is why the bromide ion have to attach to the pi complex from a different side and not the same side so that leads to the cis attack?

Thanks in advance! :smile:
 
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Due to steric effects, you'll want to observe the electron density of this reaction.
 

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