tut4 - 2. Studies of 1,2-ethanediol (HOCH 2 CH 2 OH)...

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1 CHM 138H TUTORIAL 4 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). Please work through them in preparation for Tutorial 4. Chapter 4: 4.1, 4.2, 4.5, 4.6, 4.12-4.16, 4.18, 4.26-4.37, 4.43, 4.49, 4.51, 4.53, 4.56. Of the above, the following represent some of the better questions: 4.12, 4.13, 4.16, 4.29-4.35, 4.51, 4.53, 4.56. In addition, the following problems will be discussed: 1. Ignoring compounds that contain double bonds, write structural formulas and give IUPAC names for all of the isomers with the formula C 5 H 10 . Be sure to consider whether stereoisomerism is possible!
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Unformatted text preview: 2. Studies of 1,2-ethanediol (HOCH 2 CH 2 OH) surprisingly show that the conformer in which the alcohol groups are gauche to each other is more stable than the conformer in which the alcohol groups are anti to each other. However, for 1,2-dimethoxyethane (CH 3 OCH 2 CH 2 OCH 3 ), the anti conformation is favoured, as predicted. a) Draw Newman projections for the gauche and anti conformers of 1,2-ethanediol and of 1,2-dimethoxyethane. b) Why is the gauche form of 1,2-ethanediol more stable than the anti form? Draw a picture of the important stabilizing factor. 3. Consider the trisubstituted cyclohexane molecule below. Draw the two possible chair conformations for this molecule and, explaining your reasoning, state which conformation will be more stable. CN F...
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