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Unformatted text preview: a reasonable structure for this product. 2. Write an equation, clearly showing the stereochemistry of the starting material and the product, for the reaction of ( S )-1-bromo-2-methylbutane with sodium iodide in acetone. What is the configuration ( R or S ) of the product? 3. When the dibromo compound shown below is dissolved in methanol, only one of the bromine atoms is replaced with a methoxy group. Predict the correct structure of the product and write a mechanism to explain why this product is the one formed. Hint – consider the properties of methanol as a solvent. Br Br CH 3 OH ??? 2 Here are some excellent Flashware animations to take a look at from Chapter 11: S N 2 Reaction: general mechanism S N 2 Reaction: CH 3 Cl + OH – S N 2 Reaction: 2-chlorobutane + OH – S N 2 Reaction: Williamson ether synthesis S N 1 Reaction: general mechanism S N 1 Reaction: AcO – + R 3 CCl S N 1 Reaction: tBuOH + HCl E2 Elimination E1 Elimination...
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- Spring '09
- Solvent, Diethyl ether, J. McMurry, OH– SN2 Reaction, R3CCl SN1 Reaction