Interaction | Reaction | Process     Data Page

Hydroxide ion will abstract a proton from (2R)-2-Bromopropanoic acid to give the corresponding carboxylate ion, (2R)-2-Bromopropanoate, which will undergo an internal (intramolecular) SN2 reaction, designated an SNi process, to give the corresponding alpha-lactone.

Hydroxide will ring open the optically alpha-lactone to give (2R)-2-Hydroxypropanoate. Note that the 2-Hydroxypropanoate product has the same absolute stereochemistry at its chiral centre as the 2-bromopropanoate substrate: there has been no inversion of configuration due to a neighbouring group effect.
  +  
[OH]–
         
  +  
HBr
Reactant Page Go To Go To
(2R)-2-Bromopropanoic acid     Reactions Using    Reactions Forming
Hydroxide ion     Reactions Using    Reactions Forming
(2R)-2-Hydroxy propanoate ion     Reactions Using    Reactions Forming
Hydrogen bromide     Reactions Using    Reactions Forming

Interaction, Reaction, Process defined as:
Functional Group Interconvertion
Neighbouring Group Effect
Proton transfer: Brønsted reaction
SN1, SN2 and SNi Reaction Pathways
SNi: Reactivity of (2R)-2-Bromopropanoic acid
Substitution: Nucleophilic Internal
Substitution: Nucleophilic Second Order

© Mark R. Leach 1999 –

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