CH 335 exams W07

CH 335 exams W07 - CH 335 Winter 2007 CH 335 Organic...

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CH 335 Winter 2007 CH 335 Organic Chemistry II Exam I, Winter 2007 Dr. Michael E. Koscho Name __________________________ ID # ____________________________ Place in this box the initial of your last name. INSTRUCTIONS 1. Sit in an odd numbered seat. 2. This exam is closed-book, closed-notes. 3. All exams will be collected at 12:50 pm. Pace yourself accordingly! 4. If additional space is needed on any problem, use the back-side of that sheet and indicate on the front that there is more on the back. 5. This exam is a total of seven pages (including this one and the grading sheet). Before you start, count the number of pages to be sure you have a complete exam. 6. If you have any questions, ASK ! Do not make a wrong assumption and thus lose points. 1
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CH 335 Winter 2007 1. For each of the following provide an appropriate name if given the structure, provide the structure if given the name. [2 points each] (a) OH CH 3 (b) S (c) N,N -dimethyl-2-butanamine (d) 2,3-epoxyhexane 2. For each of the following, use the letters for each compound and write your answer in the box provided. [3 points each] (a) Rank the acidity of the following compounds, from most acidic to least acidic. SH NH 2 AB C >> (b) Rank the stability of the following radicals, from most stable to least stable. >>> C D (c) Rank the basicity of the following, from most basic to least basic. Li 2 C 2
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CH 335 Winter 2007 3. For each of the following, provide the structure of the major organic product (give two products for the first reaction). Write your answer in the box provided. [3 points each] OCH 2 CH 3 HBr + OH POCl 3 pyridine Br 1) Mg / THF 2) 3) H 3 O + O Li 2) Cu I 3) 2 h ν NBS ROOR 3
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CH 335 Winter 2007 4. For each problem provide a complete curved-arrow mechanism for one of the two reactions shown (circle which one you answer). [6 points each] (a) O OH H 2 O OR O Cl NaOCH 3 CH 3 OH O OCH 3 (b) OH H 2 SO 4 CH 3 OR OH H SOCl 2 N Cl H CH 3 CH 3 CH 3 4
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CH 335 Winter 2007 5. Draw all possible mono-chlorination products for the reaction shown below (ignore stereochemistry). [5 points] CH 3 Cl 2 h ν 6. Draw the products of the reactions shown below, and briefly explain why the reactions afford different products. [8 points] HBr ROOR 7. Draw the structure of 12-crown-4-ether and the inclusion complex that forms on addition of lithium chloride. [6 points] 12-crown-4-ether 12-crown-4-ether + lithium chloride 5
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CH 335 Winter 2007 8. Provide a synthetic sequence that will afford the product indicated, beginning with the indicated starting material. Do only one of the two, and circle which one you answer. [8 points] OH OH OCH 3 OR 6
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CH 335 Winter 2007 Do not write on this page!!! Page Points Score Grader 2 17 3 21 4 12 5 19 6 8 Total (77): 7
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CH 335 Winter 2007 CH 335 Organic Chemistry II Exam II, Winter 2007 Dr. Michael E. Koscho Name __________________________ ID # ____________________________ Place in this box the initial of your last name. INSTRUCTIONS 1. Sit in an odd numbered seat. 2. This exam is closed-book, closed-notes.
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This note was uploaded on 04/07/2008 for the course CH 335 taught by Professor Koscho during the Winter '08 term at University of Oregon.

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CH 335 exams W07 - CH 335 Winter 2007 CH 335 Organic...

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