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Catalytic Allylic Alkylation quiz

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  • What two types of molecules are coupled in catalytic allylic alkylation?
    An allylic carbon and an enolate are coupled in catalytic allylic alkylation.
  • What is the main stereochemical outcome of catalytic allylic alkylation?
    The reaction is highly stereoselective, favoring the formation of one enantiomer over another.
  • What type of reaction mechanism does catalytic allylic alkylation follow?
    It follows a double SN2 mechanism.
  • How is the configuration of the chiral allylic carbon affected during the reaction?
    The configuration is retained due to two consecutive SN2 inversions.
  • What catalyst is commonly used in catalytic allylic alkylation?
    A palladium catalyst is commonly used.
  • What are common leaving groups in catalytic allylic alkylation?
    Common leaving groups include halogens (like chlorine, bromine, or iodine) and esters.
  • What is the role of the palladium complex in this reaction?
    The palladium complex facilitates the reaction and enhances its efficiency and selectivity.
  • What is the nucleophile in catalytic allylic alkylation?
    The nucleophile is an enolate group.
  • How does the palladium catalyst affect the configuration during nucleophilic attack?
    The palladium catalyst causes inversion of configuration during nucleophilic attack.
  • What happens to the configuration after the second SN2 reaction?
    The configuration is inverted back to the original, resulting in overall retention.
  • How many ligands are typically attached to palladium after the first SN2 reaction?
    There are typically two ligands attached to palladium after the first SN2 reaction.
  • What are examples of palladium catalysts used in this reaction?
    Examples include Pd(PPh3)4 and palladium(II) chloride (PdCl2).
  • Why are esters considered good leaving groups in this reaction?
    Esters are good leaving groups due to the catalytic conditions provided by palladium.
  • What is the significance of the double SN2 mechanism in this reaction?
    The double SN2 mechanism ensures retention of the original stereochemistry at the chiral center.
  • What should you review if you are unsure about enolates?
    You should review alpha carbon chemistry reactions, specifically enolates and enols.