310NSu08Midterm2Key

310NSu08Midterm2Key - Bocknack CH s310N/s318N Summer 2008...

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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 132 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 A 6 4 0 0 0 0 0 0 0 0 2 6 B 0 6 0 0 0 0 0 0 0 0 3 6 C 0 0 6 4 1 3 0 0 0 0 4 6 E 0 0 0 0 6 0 0 0 0 0 5 6 C 0 0 6 0 0 0 0 0 0 0 6 6 B 0 6 0 0 0 0 0 0 0 0 7 6 B 2 6 0 0 2 0 0 0 0 0 8 6 D 0 0 0 6 0 2 0 0 0 0 9 6 C 2 3 6 0 0 0 0 0 0 0 10 6 A 6 3 1 0 0 0 0 0 0 0 11 6 C 0 0 6 0 0 0 0 0 0 0 12 6 D 0 2 0 6 0 0 0 0 0 0 13 6 B 3 6 1 0 0 0 0 0 0 0 14 6 D 0 0 2 6 0 0 0 0 0 0 15 6 A 6 0 1 0 2 0 0 0 0 0 16 6 C 1 2 6 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 0 6 0 0 0 0 0 0 0 0 20 6 D 0 0 0 6 0 0 0 0 0 0 21 6 C 2 0 6 0 0 0 0 0 0 0 22 6 D 0 0 0 6 0 0 0 0 0 0 1 Bocknack CH s310N/s318N – Summer 2008 MIDTERM EXAM #2 ANSWER KEY
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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 !!! 23. (24 points) Compound A , having molecular formula C 8 H 14 O 4 , has the IR and 1 H NMR spectra given below. 13 C NMR data is provided below the IR spectrum: When A is exposed to concentrated aqueous potassium hydroxide, followed by dilute aqueous acid, Compound B (C 4 H 6 O 4 ) is formed. Two equivalents of ethanol are also formed as a result of this reaction. When B is treated with 2 equivalents of SOCl 2 , Compound C (C 4 H 4 Cl 2 O 2 ) is produced. When C is reacted with 2 equivalents of (CH 3 ) 2 CuLi, Compound D (C 6 H 10 O 2 ) is formed. If D is treated with I 2 , KOH, H 2 O, followed by dilute aqueous acid, B is obtained, along with a yellow solid precipitate. Compounds A , B , C , and D are all achiral. Propose structures for Compounds A , B , C , and D by completing the reaction scheme given below. It is not necessary to show stereochemistry in the structures that you draw, nor is it necessary to explain your answers. 8
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This note was uploaded on 09/14/2009 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas.

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310NSu08Midterm2Key - Bocknack CH s310N/s318N Summer 2008...

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