Interactions | Reactions | Processes

Classified as: SNi: Reactivity of (2R)-2-Bromopropanoic acid

The (2R)-2-Bromopropanoate ion forms a transient alpha-lactone ring which is ring opened with hydroxide.

The double SN2 substitution, and hence x2 Walden inversion, results in retention of configuration at the chiral centre.
  +  
[OH]–
         
  +  
H2O

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  +  
Br–

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  +  
[OH]–
         

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  +  
[OH]–
         
  +  
HBr

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© Mark R. Leach 1999 –

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