Chemistry · General methods of preparation, properties and reactions, nature of C-X bond, mechanisms of substitution reactions

Which of the following halogen exchange reaction will occur in acetone?

Which of the following halogen exchange reaction will occur in acetone?

  • A. \( R-I+N a C l \rightarrow \)
  • B. \( R-F+K C l \rightarrow \)
  • C. \( R-C l+N a l \rightarrow \)
  • D. \( R-F+A g B r \rightarrow \)

Step-by-step solution

In acetone, a polar aprotic solvent, the Finkelstein reaction occurs: alkyl chlorides react with sodium iodide to form alkyl iodides, driven by the precipitation of NaCl. Option A is unfavorable because iodide is a better leaving group; options B and D involve poor leaving groups (fluoride) or insoluble salts. Thus, only option C proceeds.
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