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O. Chemistry (Nucleophilic Substitution)

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1. Explain why the reagent NaI in acetone encourages SN2 reactions. Provide another nucleophile/solvent combination that encourages SN2. What characteristics will each have?

2. Write the complete mechanism for the reaction of (3S, 4R) 3-bromo-3,4-dimethylhexane with methanol. Will this be an SN1 or SN2 reaction? Use wedge-dash notation to show the products.

For the first part of the first question, is it enough to say that I anion is an excellent nucleophile and acetone has limited ability to stabilize carbocation intermediates? Also, NaI is soluble in acetone. But when the leaving group is either Br or Cl in an SN2 reaction, NaBr or NaCl precipitates as an
insoluble salt?

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