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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 SN2 reaction has occurred with inversion of configuration
B) racemization followed by an SN2 attack
C) an SNI reaction has taken over resulting in inversion of configuration
D) an SN1 reaction has occurred due to carbocation formation
E) an SN1 reaction followed by an SN2 "backside" attack

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