The nucleophilic substitution reaction of sodium 2-bromopropanoate with water shown in Problem 11.35 occurs with retention of configuration at very low NaOH concentrations, but occurs with inversion of configuration at 1 M NaOH. Relate this finding to your answers for Problem 11.35.

Problem 11.35

The nucleophilic substitution reaction of sodium 2-bromopropanoate with water and/or –OH can occur by both an S_N2 (intermolecular) mechanism and a mechanism that involves neighboring-group participation.

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H₂C-CH-C-0 Na+ Nat-OH ₁&o 1 Br sodium 2-bromopropanoate H₂O H₂C-CH-C-0 Na+ Na Br C-CH-i-o- T OH sodium lactate