1 CHE 230-002 Organic Chemistry Exam 1 Make-Up #2, 2011 Name ______________________ Student ID No. ___________________ Before you begin this exam: First: You are allowed to have a simple model set at your seat. Please put away all other materials. Second: Place your student identification on your desk. A proctor will come around to check everyone’s ID. Third: Read through the entire exam. Your goal, as always, is to score as many points as possible. Do not waste time on problems that you can’t do if there are others that look easy. Fourth: READ EACH QUESTION CAREFULLY. Be sure you answer the question that is asked. Fifth: Once the start time is announced, you have one hour to complete this exam. There will be no extensions, so budget your time carefully. Problem Number Points Possible Score 1. 20 _____________ 2. 15 _____________ 3. 15 _____________ 4. 15 _____________ 5. 30 _____________ 6. 15 _____________ 7. 15 _____________ 8. 10 _____________ 9. 15 _____________ 10. 5 _____________ 11. 10 _____________ 12. 15 _____________ 13. 10 _____________ 14. 10 _____________ Total 200 _____________2 1. (15 points) Insert lone pair electrons, single bonds, double bonds, and/or triple bonds in the neutral structures below in an arrangement that gives no formal charges on any atom. Assume connectivity as implied by atom position. 2. (20 points) All lone pairs and and atoms are drawn in the structures below. Label any formal charges. If there are no formal charges in a given structure, write the word “none” below the structure. ________________ ______________ ___________ ___________ 3. (15 points) Predict the geometry (in words, not degrees or hybridization) at each indicated C atom. ________________ ______________ ______________ BCCHOHHHC CHHNHHCH HHHHHNH2CNOH3COHHBHHHHNH2NH2NH23 4. (15 points) Draw a Lewis structure for the following neutral skeletal structures. Include implied C and H atoms and implied lone pairs. 5. (30 points) Using curved arrow notation and the appropriate arrow between structures, draw the second best resonance structure for each of the molecules drawn below. BNBNBNOHCH3CH3ClCl4 6. (15 points) Draw the skeletal structures for molecules with the following names. Do not include implied C and H atoms. 1,3,5-trimethylcycloheptane 2-hydroxypentane 1,2-dimethypropane 7. (15 points) Draw neutral skeletal structures from each condensed structure that do not have formal charges. Do not include implied lone pairs. Do not include implied C and H atoms or implied bonds. (CH3(CH2)4)3N (CH3(CH2)2)2O CH3CH2COOH 8. (10 points) Draw one skeletal structure for each the following. There may be more than one correct answer. If you draw more than one answer, only the first answer will be graded. (a) an ester with the formula C6H12O2 (b) an alkane with the formula C5H105 9. (15 points) Identify the circled functional groups in amixicillin, an antibiotic. 10. (5 points) How many degrees of unsaturation are in 1-cyano-2-methylbenzene, shown below? __________________ CCH3N6 11. (10 points) Draw 4 constitutional isomers of cyclohexene, shown below. If you draw more than 4 isomers, only the first 4 will be graded. None of your answers should be stereoismoers of each other. 12. (15 points) Label the following pairs of structures as constitutional isomers, enantiomers, diastereomers, the same, or neither. CH3CH3CH3CH3OOH7 13. (10 points) Mark each C atom as “stereogenic” or “nonstereogenic.” For any stereogenic C atom(s), label them as R or S. 14. (10 points) From the Newman Projection shown below, draw the corresponding skeletal structure. Implied C atoms and lone pairs should not be included. Implied H atoms should only be included to assist in identifying stereocents. Include wedges and dashes only when they are needed to show stereochemistry. END OF EXAM
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