Discussion Worksheet Chapter 12

Discussion Worksheet Chapter 12 - after treatment with...

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Chapter 12 Worksheet Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant. 1. 2. 3. 4. 5. 6. Done by Dr. Felix N. Ngassa for CHM 242: Organic Chemistry for Life Sciences 2, GVSU, Spring/Summer 2011. 1 C C H H 1. OsO 4 , pyridine 2. NaHSO 3 , H 2 O 1. O 3 , CH 2 Cl 2 2. Zn, HOAc CH 3 KMnO 4 H 3 O + CH 3 CH 2 C C CH 3 D 2 Lindlar catalyst KMnO 4 H 3 O + CH CH C C H excess H 2 Pd/C
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To answer the questions below consider the following information: In an abandoned laboratory has been found a flammable liquid, A, in a bottle bearing only the label “Compound A: C H 7 12 .” Government agents have offered you a considerable sum to determine the structure of this compound. After verifying the molecular formula by elemental analysis, you find that Compound A reacts with 1 mol equiv of hydrogen and, after treatment with acidic KMnO 4 , gives the dicarboxylic acid C (see below). Another bottle from the same laboratory is labeled “Compound B (isomer of A).” Compound B also reacts with 1 mol equiv of hydrogen, but yields cyclohexanone
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Unformatted text preview: after treatment with acidic KMnO 4 . 7. How many degrees of unsaturation does Compound A possess? 8. Suggest structures for A and B. 9. What was the other product formed in the KMnO 4 oxidation of B? Done by Dr. Felix N. Ngassa for CHM 242: Organic Chemistry for Life Sciences 2, GVSU, Spring/Summer 2011. 2 HO C O CHCH 2 CH 2 CH 2 CH 3 C O OH Compound C O cyclohexanone 10. Complete the synthetic sequence below by drawing the structures of the reaction in the boxes provided. 11. Using acetylene and any alkyl halides as starting materials, synthesize the following compound. More than one step may be required. Show all reagents and all intermediate compounds in your synthetic scheme. Done by Dr. Felix N. Ngassa for CHM 242: Organic Chemistry for Life Sciences 2, GVSU, Spring/Summer 2011. 3 CH 3 CHCH 2 CH 2 CH 3 Br Br 2 H 2 O NaOH NaOCH 3 CH 3 OH PCC CH 2 Cl 2 C 8 H 14 O 2...
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