Practice question
Question
Which intermediate is most stabilized by the inductive effect of alkyl groups in CH₃CH₂CH(CH₃)CH₂Cl upon heterolytic cleavage?
Explanation
Heterolytic cleavage of CH₃CH₂CH(CH₃)CH₂Cl at CH₂Cl forms CH₃CH₂CH(CH₃)CH₂⁺ (primary), but a hydride shift forms CH₃CH₂C⁺(CH₃)CH₃ (tertiary), stabilized by the +I effect of three alkyl groups.
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