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1. Neighboring group participation can result in two different stereochemical outcomes in the solvolysis of α-bromopropionate depending on the concentration of hydroxide ion. 2. In concentrated hydroxide, the reaction proceeds by a straightforward SN2 mechanism, resulting in inversion of configuration. 3. In dilute hydroxide, neighboring group participation of the carboxylate group leads to initial inversion, followed by a second SN2 step, resulting in retention of configuration. 4. Neighboring group part

Author

Andri A. Liem

Language

EN