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Exam 3 - April 24th 2002 Page 1 of 14 April 24th 2002 Dr S...

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April 24th, 2002 Dr. S. A. Dandekar CHEM 2370 Exam 3 (100 points) Name _________________________ Select the best answer from the given choices for ANY 28 of questions 1- 32. You may do more than the required number of questions if you wish. 1. What is the simplest alkene, i.e., the one with the smallest molecular weight, which can exhibit optical activity? a. 3-methyl-1-pentene b. 3-methyl-2-pentene c. 4-methyl-1-pentene d. 3-methyl-1-butene e. 4-methyl-2-hexene 2. One mol of each of the following alkenes is subjected to complete combustion. Which would you expect to liberate the least heat? 3. Which of the following carbocations would be likely to undergo rearrangement? + | CH 3 | CH 3 ——CH——C——CH 3 + | CH 3 | CH 3 ——C——CH 2 ——CH 3 + Page 1 of 14 April 24th, 2002 1/19/2007 http://www.chem.unt.edu/CHEM2370/2370EX3.htm
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Exam 3 (100 points)--Page 2 4. Which mechanistic step in the acid-catalyzed dehydration of 3,3-dimethyl-2-butanol is the rate determining step? | | CH 3 ——C———CH——CH 3 + H 3 O + ‹===› CH 3 ——C———CH——CH 3 + H 2 O | | | | CH 3 OH CH 3 OH 2 + | | CH 3 ——C———CH——CH 3 === › CH 3 ——C———CH——CH 3 + H 2 O | | | + CH 3 OH 2 CH 3 + | | CH 3 ——C——CH——CH 3 === › CH 3 ——C——CH——CH 3 | + + | CH 3 CH 3 | CH 3 ——C——CH——CH 3 + H 2 O ‹===› (CH 3 ) 2 C C(CH 3 ) 2 + H 3 O + + | CH 3 5. Rearrangements are likely to occur in which of the following reaction types? a. S N 1 reactions b. S N 2 reactions c. E1 reactions d. E2 reactions e. Both S N 1 and E1 reactions
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