Reaction of (R)-2-Chloro-4-Methylhexane with Excess NaI in Acetone Gives Racemic

question 11

Multiple Choice

Reaction of (R) -2-chloro-4-methylhexane with excess NaI in acetone gives racemic 2-iodo-4-methylhexane.What is the explanation that best describes this transformation?

• A)an S_N2 reaction has occurred with inversion of configuration
• B)racemization followed by an S_N2 attack
• C)an S_NI reaction has taken over resulting in inversion of configuration
• D)an S_N1 reaction has occurred due to carbocation formation
• E)an S_N1 reaction followed by an S_N2 "backside" attack

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