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1 ANSWER KEY Page 1 of 7 University of Manitoba Department of Chemistry Introductory rganic Chemistry II Term Test 1 Thursday February 5, 2003 This is a 2-hour test, marked out of 50 points total. Part marks are available on all questions. Put all answers in the spaces provided. If more space is required you may use the backs of the exam pages but be sure to indicate that you have done so. A table of spectroscopic data is attached at the end of the exam. 1. (8 MARKS) Provide a detailed stepwise mechanism for the following Friedel-Crafts acylation reaction, showing all the steps. Make sure your mechanism clearly illustrates why the major product has the para regiochemistry. Al 3 /C 2 2 C 3 major product + Al 3 Al 3 C Al 4 3 C 3 C 3 C 3 C cation is stabilized by donation of oxygen lone pairs C
2 ANSWER KEY Page 2 of 7 2. (7 MARKS) Provide a detailed, stepwise mechanism for the following transformation. Show all steps (1,2-shift)
3 ANSWER KEY Page 3 of 7 3. (10 MARKS) Provide a rationalization for the observation that it is possible to achieve a successful synthesis of para-t-butylbenzenesulfonic acid under the conditions of the first reaction sequence but not under the conditions of the second reaction sequence. Give the product you predict would be formed by the second reaction sequence. 1. t-butyl chloride Fe 3 Successful synthesis 2. Fuming 2 S 4 S 3 1. Fuming 2 S 4 2. t-butyl chloride Fe 3 Unsuccessful synthesis S 3 In the first sequence, Friedel-Crafts alkylation occurs before sulfonation. The product of the first step is t-butylbenzene. The alkyl group is an ortho/para director, so that the sulfonation step occurs at the para position. The ortho position is disfavored by the steric bulk of the t-butyl group. In the second sequence, sulfonation is performed first. The product here is benzenesulfonic acid. The sulfonic acid group is strongly electron-withdrawing, and so the attempted Friedel-Crafts alkylation in the second step will not occur. Friedel-Crafts alkylations require electron-rich aryl rings. The product of the second sequence overall is therefore benzenesulfonic acid. S
4 ANSWER KEY Page 4 of 7 4. (20 MARKS) Provide the necessary product, reagent/solvent or starting material to correctly complete the following reactions. Mechanisms are NT required. B 2 6, TF then 2 2, Na (aq) Include an appropriate a. workup for this reaction 2 N C N 3 / 2 S 4 N C N b. Br Br, AlBr 3 C 2 2 Br NC c. NC 1. 3 (g) C 2 2, -78 o C C 2 3 C 2. Zn, Ac 3 C d. C 3 e. C 2 2
5 ANSWER KEY Page 5 of 7 3 C + heat f NN 2 Na heat g. 2. Br 2 /AlBr 3 Br 2 S 4 h. 3 C N C N 2. Na 2 C 3 3 C i. 3 C C 2 I 2, Zn 3 C j.
6 ANSWER KEY Page 6 of 7 5. (5 MARKS) An unknown organic molecule with the molecular formula C gave the following IR, 13 C and 1 NMR spectra. What was the structure of the unknown? PPM Expansion of ppm region 3 C 3 C 3 C C ,4,5-Trimethyl-benzaldehyde This isomer is also acceptable for full marks Structure of Compound A: 3 C C ,4,6-Trimethyl-benzaldehyde
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