Consider the reaction of 2-bromobutane (where the stereocenter is in the \"R\" c
ID: 103221 • Letter: C
Question
Consider the reaction of 2-bromobutane (where the stereocenter is in the "R" configuration) with OH. How many of the following statements are true? 1. If the reaction proceeds through an SN1 mechanism two alcohol products will be formed 1 "R" and 1 "S" 2. If the reaction goes through an SN1 mechanism it means the pathway for secondary carbocation formation was higher in energy than the pathway for the attack of a nucleophile on the secondary alkyl halide 3. An mixture of the R and S isomers would indicate the reaction proceeded through a second order process 4. The reaction could proceed through either an SN1 or SN2 mechanism. Information about the stereochemistry of the reaction or rate law would be needed to determine which mechanism was used 5. If the reaction proceeds through an SN2 mechanism one alcohol product will be formed, the "S" isomerExplanation / Answer
For the reaction of (R)-2-bromobutane,
true statement would be,
3
The Sn2 reaction of alkyl bromide yields inversion of configuration at chiral center, so we would get S-alcohol. The Sn1 reaction proceeds through a planar carbocation intermediate, therefore products could be both R adn S alcohols. The secondary alkyl halide may undergo both Sn1 or Sn2 reaction, only reaction rate law can confirm the actual mechanism.