Interaction | Reaction | Process     Data Page

The sodium reacts with the solvent, ethanol, to produce sodium ethoxide and hydrogen.

The sodium ethoxide abstracts a proton from the methylene function producing a nucleophile which displaces bromide.

A second ethoxide pulls off the second acidic methylene proton producing a second carbanion which reacts in an intramolecular manner with the second bromide to close the ring.

Organic Syntheses, CV3, 213 (1955)
  +  
  +  
2
Na
  +  
CH3CH2OH
         
  +  
2
NaBr
  +  
H2
Reactant Page Go To Go To
1,3-Dibromopropane     Reactions Using    Reactions Forming
Diethyl malonate     Reactions Using    Reactions Forming
Sodium     Reactions Using    Reactions Forming
Ethanol Solvent    Reactions Using    Reactions Forming
Methyl 1-methoxycarbonylcyclobutanecarboxylate     Reactions Using    Reactions Forming
Sodium bromide     Reactions Using    Reactions Forming
Hydrogen     Reactions Using    Reactions Forming

Interaction, Reaction, Process defined as:
Proton transfer: Brønsted reaction
Substitution: Nucleophilic Second Order

© Mark R. Leach 1999 –

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