What is the mechanism of the reaction between an alkyl halide and a nucleophile

Practice Questions

Q1
What is the mechanism of the reaction between an alkyl halide and a nucleophile in a bimolecular nucleophilic substitution (SN2)?
  1. Nucleophile attacks from the back side, leading to inversion of configuration
  2. Nucleophile attacks from the front side, leading to retention of configuration
  3. Formation of a carbocation intermediate
  4. Nucleophile attacks the halogen first

Questions & Step-by-Step Solutions

What is the mechanism of the reaction between an alkyl halide and a nucleophile in a bimolecular nucleophilic substitution (SN2)?
  • Step 1: Identify the alkyl halide, which has a carbon atom bonded to a halogen (the leaving group).
  • Step 2: Identify the nucleophile, which is a species that has a lone pair of electrons and can donate them to form a bond.
  • Step 3: The nucleophile approaches the carbon atom of the alkyl halide from the side opposite to the halogen (the leaving group).
  • Step 4: As the nucleophile gets closer, it begins to form a bond with the carbon atom, while the bond between the carbon and the halogen starts to break.
  • Step 5: The nucleophile fully bonds to the carbon atom, and the halogen leaves as a separate ion (the leaving group).
  • Step 6: This process results in the inversion of configuration at the carbon atom, meaning the spatial arrangement of the groups around the carbon changes.
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