The given benzylic iodide is inert toward S_N1 and S_N2 reactions. Explain why.

• A. The S_N1 reaction is not possible because a bridgehead carbocation can not be formed due to high angle and ring strains.
  The S_N2 reaction is not possible because of the high steric hindrance for the backside attack of the nucleophile.
• B. The S_N1 reaction is not possible because tertiary benzylic carbocations are not stable.
  The S_N2 reaction is not possible because of the high steric hindrance for the backside attack of the nucleophile.
• C. The S_N1 reaction is not possible because the resulting carbocation would be in conjugation with the ring.
  The S_N2 reaction is not possible because the incoming nucleophile would attack the benzene ring instead.
• D. The S_N1 and S_N2 reactions are not possible because iodide is a poor leaving group.

Answer: (A)