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Tutorial 10 - a reasonable structure for this product 2...

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1 CHM 138H TUTORIAL 10 As described in the course outline, the tutorial quizzes will be based closely upon the textbook questions recommended below for this week's tutorial as well as those recommended in last week's tutorial. You should be able to do the questions below from the course textbook (J. McMurry, 7 th Edition): Chapter 11: 11.1-11.6, 11.8, 11.11-11.13, 11.25-11.27, 11.29-11.31, 11.33, 11.36-11.45, 11.56, 11.64-11.65, 11.68-11.69. Of the above, the following represent some of the better questions: 11.33, 11.41, 11.42, 11.44, 11.45, 11.56, 11.64, 11.65, 11.68. In addition, the following problems will be discussed, which focus on Chapter 11 material and concepts discussed in lecture: 1. Reaction of ethyl iodide with triethylamine, (CH 3 CH 2 ) 3 N, yields a crystalline compound C 8 H 20 NI in high yield. This compound is soluble in polar solvents such as water but insoluble in non-polar ones such as diethyl ether (CH 3 CH 2 OCH 2 CH 3 ). It does not melt below 200 o C. Suggest
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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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