07_Final_266

07_Final_266 - Fall 2007 Chem 266 1 Course Number Course...

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Fall 2007 Chem 266 1 Course Number CHEMISTRY 266 Course Title INTRODUCTORY ORGANIC CHEMISTRY Instructors X. FANG, S. FORSEY Date of Exam December 18, 2007 Time Period 4:00 – 6:30 Duration of Exam 2.5 HOURS Number of Exam Pages (including this cover sheet) 17 Exam Type CLOSED BOOK Additional Materials Allowed CALCULATORS, MOLECULAR MODELS INSTRUCTIONS 1. On the computer card, fill in the best choice A to E for each of the 55 questions which follow. 2. There is 1 mark for a correct answer and 0 mark for an incorrect or missing answer. 3. Under ID number, put your ID number. 4. Under Section, leave blank. 5. Under Test Master, leave blank. 6. Remember to put your name and ID number on the right. 7. Calculators and/or molecular model kits may be used by individual students but may not be shared around during the examination period. 8. Make certain that all of your answers are properly indicated on the computer card. Only the answers marked on the computer card will be considered in arriving at your final exam mark. Do not submit the question papers. 9. The following abbreviations may appear: D = deuterium, 2 H Et = ethyl, C 2 H 5 Me = methyl, CH 3 Ph = phenyl, C 6 H 5 Ac = acetyl, CH 3 C(O) t -Bu = tertiary butyl 10 A Periodic Table of the Elements and a pKa table appear on the last page of this examination.
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Fall 2007 Chem 266 2 1. Which of the followings cannot be a correct Lewis structure? (note charges have not been shown) A) B O H H H B) N O O H C) C O H Cl D) C N H N H 2. How are the following molecules related? Br Br Cl A) enantiomers B) diastereomers C) meso compound D) same compound 3. Which of the following compounds would have the highest boiling point? A CH 3 CH 2 CH 2 OH B CH 3 CH=CHCH 3 C) CH 3 COCH 3 D CH 3 CH 2 CHO E CH 3 CH 2 CH 2 NH 2 4. Which of the following compounds has the lowest p K a value? H H H H H CH 3 H H 3 H 3 5. List the following acids from strongest to weakest 1) HF 2) HBr 3) CH 3 CF 2 CH 2 OH 4) CH 3 CBr 2 CH 2 OH A) 1 > 2 > 3 > 4 B) 1 > 2 > 4 > 3 C) 2 > 1 > 3 > 4 D) 2 > 1 > 4 > 3 E) 3 > 2 > 4 > 1
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Fall 2007 Chem 266 3 6. Which of the following is the least important resonance structure? O H Br H O H Br H H 3 CO H 3 O H Br H H 3 O H Br H H 3 O H Br H H 3 A) B) C) D) E) 7. Which of the following radicals is the most stable? C H C H CH 3 C 3 3 2 CHCH 3 A) B) C) 2 2 2 8. Which functional group is not present in the anticancer compound Taxol? A) phenyl B) ketone C) alcohol D) ester E) amine 9. Each of the following molecules contains two halogen atoms of different kinds. They are either at different positions in the molecule or are different halogen atoms entirely. In each case which halogen would be more reactive in an S N 1 reaction? A) 1, 3, 5 B) 2, 4, 6 C) 1, 4, 5 D) 2, 3, 6 E) 1,3,6 Br Br Cl Br (1) (2) (3) (4) (5) (6)
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Fall 2007 Chem 266 4 10. Predict the major product for the following reaction: KMnO 4 OH - major product (cold) OH O OH O O O A) B) C) D) E) 11. The relationship for the following two compounds is: CH 3 Cl Br 2 3 3 2 3 A) enantiomers B) diastereomers C) a meso compound D) the same E) different conformations of the same compound 12. How many chiral carbons are found in ( S )-adenosylmethionine?
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07_Final_266 - Fall 2007 Chem 266 1 Course Number Course...

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