Consider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with sodium methoxide. Which of the following would be true? A) An SN2 reaction would... Consider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with sodium methoxide. Which of the following would be true? A) An SN2 reaction would take place with inversion of configuration at the stereogenic center. B) An SN1 reaction would take place with retention of configuration at the stereogenic center. C) An SN1 reaction would take place with racemization of configuration at the stereogenic center. D) An SN1 reaction would take place, accompanied by an E1 reaction, affording a complex mixture of products. E) An E2 reaction would take place, during which the stereogenic center is lost.
Understand the Problem
The question asks about the type of substitution reaction that occurs when (R)-3-bromo-3-methylhexane is treated with sodium methoxide, focusing on the stereochemical implications of the reaction.
Answer
An SN1 reaction would take place with racemization of configuration at the stereogenic center.
The reaction that would most likely occur is SN1 with racemization of configuration at the stereogenic center.
Answer for screen readers
The reaction that would most likely occur is SN1 with racemization of configuration at the stereogenic center.
More Information
The steric hindrance on the tertiary carbon favors the SN1 mechanism, leading to a mixture of products with racemization.
Tips
A common mistake is to assume an SN2 reaction will occur because of the strong nucleophile, but steric hindrance prevents it.
Sources
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