In a typical nucleophilic substitution reaction, what type of bond cleavage occurs when the leaving group departs from the substrate?
A
Homolytic bond cleavage
B
No bond cleavage occurs
C
Both heterolytic and homolytic bond cleavage
D
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Understand the nature of bond cleavage: Bond cleavage can occur in two main ways—homolytic and heterolytic. Homolytic cleavage results in each atom retaining one electron, forming radicals, while heterolytic cleavage results in one atom retaining both bonding electrons, forming ions.
In a nucleophilic substitution reaction, the leaving group departs from the substrate by breaking the bond between them. Consider what happens to the bonding electrons during this process.
Since the leaving group takes both electrons from the bond when it leaves, this indicates that the bond breaks unevenly, producing a negatively charged leaving group (an anion) and a positively charged or neutral substrate intermediate.
This uneven breaking of the bond, where one atom takes both electrons, is characteristic of heterolytic bond cleavage.
Therefore, the type of bond cleavage occurring when the leaving group departs in a nucleophilic substitution reaction is heterolytic bond cleavage.