Exam_1_06 - ” CH(CH 3 2 a b c O O C CH 3 H H(H 3 C 2 HC O...

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1 Spring 2006, CEM252 Exam 1 (100 Points) 1. (9 Points, 3 points each box) Give the correct structures for the following compounds. a) m- isopropoxytoluene b) Phenyl formate c) d -Valerolactone
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2 2. (9 Points, 3 point each) Give the proper systematic or common name for each of the following compounds. C O Cl Br a) b) Ph(CH 2 ) 5 CO 2 H c) O O O 3. (4 Points) Draw the splitting diagram for H a in the following molecule. SPh H c H b H a J ab = 1.9 Hz J ac = 14.1 Hz J cb = 9.2 Hz
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3 4. (12 Points, 2 points each box) In the boxes provided, indicate the number of 1 HNMR signals and 13 CNMR signals each of the following compounds. OH HO O H O O H 1 HNMR 1 HNMR 1 HNMR 13 CNMR 13 CNMR 13 CNMR A B C 5. (6 Points, 3 point each) Encircle the more stable carbocation in each pair. Br NO 2 NO 2 Br or NO 2 Br Br NO 2 or a) b) 6. (6 Points) Which of the following five compounds is responsible for the IR spectrum given below?
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4 7. (9 Points, 3 point each) Give the expected multiplicity (i.e. singlet, doublet, etc.) of 1 HNMR signals for protons indicated with an “
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Unformatted text preview: * ”. CH(CH 3 ) 2 a) * b) c) O O C CH 3 H H * (H 3 C) 2 HC O CH 3 H * 8. (10 Points) Deduce the structure of the following compound with a molecular formula of C 9 H 11 Br. 1 HNMR: At 7.3 ppm, multiplet, 5 H 3.4 ppm, triplet, 2 H 2.8 ppm, triplet, 2 H 2.2 ppm, quintet, 2 H 5 9. (8 Points) Outline an efficient synthesis for the following starting with benzene and any other necessary reagents. NO 2 ? CO 2 H 6 10. (27 Points, 3 points each box) Complete the following reactions by filling the boxes with the appropriate reagents, reactant(s), or product(s). For the products, only include the major organic products. Cl O CH 3 NH 2 2 1) 2) Pd, H 2 a) b) Cl NH 2 c) 1) NaNO2, HCl, 0 o C 2) CuCN 7 Cl O 1) 2) NH 2 NH 2 , H 2 O, KOH d) e) CH 3 f) 1) NBS, Peroxide, heat , FeCl3 OCH 3 O O Cl 2) Mg, ether 3) O 4) H 3 O (NBS= N-bromosuccinimide)...
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