310NSp08Exam3Key - Bocknack CH 310N Spring 2008 MIDTERM...

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How to read this table : In the first three columns, you’ll find the question number, the maximum points possible, and the correct answer choice. The columns labeled “A” through “J” indicate the points awarded for the problem if this letter was the choice indicated on the answer sheet. Please check the Blackboard gradebook to see how you answered the Part I questions, and to check your raw score (out of 150 points possible) for Part I of the exam. Part I answer sheets will not be returned, and no regrades are possible on Part I of the exam!!! Question Max. Points Correct A B C D E F G H I J 1 6 B 0 6 0 0 0 0 0 0 0 0 2 6 F 0 0 0 0 0 6 0 0 0 0 3 6 D 0 0 0 6 0 0 0 0 0 0 4 6 C 0 0 6 0 0 0 0 0 0 0 5 6 B 0 6 0 0 0 0 0 0 0 0 6 6 E 0 0 0 0 6 3 0 0 0 0 7 6 A 6 0 0 0 0 0 0 0 0 0 8 6 D 0 0 3 6 0 0 0 0 0 0 9 6 B 0 6 0 0 0 0 0 0 0 0 10 6 G 2 2 2 4 4 4 6 0 0 0 11 6 B 0 6 0 2 2 2 0 0 0 0 12 6 A 6 0 0 0 0 0 0 0 0 0 13 6 C 0 0 6 0 0 0 0 0 0 0 14 6 D 0 0 0 6 0 0 0 0 0 0 15 6 C 0 0 6 0 0 0 0 0 0 0 16 6 B 0 6 0 0 0 0 0 0 0 0 17 6 A 6 0 0 0 0 0 0 0 0 0 18 6 B 0 6 0 0 0 0 0 0 0 0 19 6 B 2 6 0 2 0 0 0 0 0 0 20 6 C 0 2 6 3 0 0 0 0 0 0 21 6 C 0 0 6 0 0 0 0 0 0 0 22 6 D 0 0 0 6 0 0 0 0 0 0 23 6 B 0 6 2 0 0 0 0 0 0 0 24 6 A 6 0 0 0 0 0 0 0 0 0 25 6 C 0 0 6 0 0 0 0 0 0 0 Bocknack CH 310N – Spring 2008 MIDTERM EXAM #3 ANSWER KEY
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10 Part II – Write your answers to all questions on this page in the space provided. If you use a pen, only blue or black ink is acceptable!!! PLEASE READ EACH QUESTION VERY CAREFULLY !!! 26. (20 points) Compound A has molecular formula C 7 H 12 O 4 . The 1 H and 13 C NMR spectra of Compound A are given at the top of Page 9. When A is treated first with NaOEt in EtOH solvent, followed by CH 3 CH 2 Br, Compound B (C 9 H 16 O 4 ) is formed as the major product. When B is treated first with aqueous NaOH, followed by an acid workup with heating, C (C 4 H 8 O 2 ) is produced. This reaction also produces CO 2 gas and 2 equivalents of CH 3 CH 2 OH. The IR spectrum of Compound C is given in the middle of Page 9. When C is treated with diazomethane (CH 2 N 2 ), D (C 5 H 10 O 2 ) is isolated as the major product. The 1 H and 13 C NMR spectra of
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This note was uploaded on 04/30/2008 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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310NSp08Exam3Key - Bocknack CH 310N Spring 2008 MIDTERM...

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