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(Solved) 80. What would be the major product(s) of the following reaction?


In the following problem, the answer key says B, which would indicate an SN2 mechanism. This would mean a strong nucleophile and a weak base, which NaI qualifies as. However, acetone has a pKa of around 19, making it a strong base. A strong base with a strong nucleophile would instead indicate an E2 mechanism. Assuming the answer key is correct, how do I discount the strong base of acetone when deciding to choose SN2 over E2?

80. What would be the major product(s) of the following reaction?
Br NaI
—> Acetone A) I B) 11 C) 111 D) IV E) None of the above

 


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