Question 14 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI 19 18 17 16 Pd or Pt (catalyst) 20 1 2 HBr ROOR (peroxide) H₂O H₂SO4 HCI 6 1. BH3.THF 2. H₂O2, NaOH 12 11 10 MCPBA 1. Os04 2. H₂O2 CH3CO₂H (peroxyacid) 15 14 13 A B Pd or Ni (catalyst) D2 (deuterium) Br2 Br2 H₂O BH3⚫THF C D OH OH OH OH OH OH OH "OH "OH OH OH OH OH OH OH OH OH OH OH "OH A B ° C D

Question 14 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI 19 18 17 16 Pd or Pt (catalyst) 20 1 2 HBr ROOR (peroxide) H₂O H₂SO4 HCI 6 1. BH3.THF 2. H₂O2, NaOH 12 11 10 MCPBA 1. Os04 2. H₂O2 CH3CO₂H (peroxyacid) 15 14 13 A B Pd or Ni (catalyst) D2 (deuterium) Br2 Br2 H₂O BH3⚫THF C D OH OH OH OH OH OH OH "OH "OH OH OH OH OH OH OH OH OH OH OH "OH A B ° C D

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Question 17 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. A Bra CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI 18 17 16 15 14 mCPBA 1. OsO4 2. H₂O₂ CH3CO₂H (peroxyacid) B 12 Pd or Pt (catalyst) 20 1 2 HBr ROOR (peroxide) H₂O H₂SO4 HCI 1. BH3.THF 13 12 11 10 9 2. H₂O2, NaOH Br2 Pd or Ni (catalyst) Br₂ H₂O BH3⚫THF с D OH OH OH OH OH OH ""OH "OH OH OH OH OH OH œ œ œ œ œ OH "OH OH OH OH 'OH A B ос D
Question 15 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. (CH3)2S Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI Pd or Pt (catalyst) 20 1 2 19 18 17 16 15 14 13 12 11 10 MCPBA 1. OsO4 2. H₂O₂ CH3CO₂H (peroxyacid) MCPBA HBr ROOR (peroxide) H₂O H2SO4 HCI 1. BH3.THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF Br2 FIOH Pd or Ni (catalyst) D₂ (deuterium) A B с 000 ABCD ....O D
Question 13 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Brz CH3OH 1.03 2. DMS KMnO4, NaOH cold HI 19 18 17 16 15 14 13 Pd or Pt (catalyst) 201 MCPBA 1. OsO4 2. H₂O₂ CH3CO₂H (peroxyacid) MCPBA 2. H₂O+ HBr ROOR (peroxide) H₂O 9 12 11 10 Pd or Ni (catalyst) D₂ (deuterium) FIOH H2SO4 HCI 1. BH3⚫THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF A B с D Α В ABCD OH "OH ४.४
Question 18 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Br2 CH₂OH 1.03 18 17 16 15 14 13 19 2. DMS KMnO4, NaOH cold HI mCPBA 1. OsO4 2. H₂O₂ CH CO;H (peroxyacid) MCPBA 2. H₂O Pd or Ni (catalyst) D2 (deuterium) 12 11 10 Pd or Pt (catalyst) 8 HBr ROOR (peroxide) H₂O H2SO4 HCI 1. BH3.THF 2. H₂O2, NaOH Br2 H₂O BH3⚫THF Br2 O A B A OH ein C U D ОН B D
Question 5 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Br2 2. (CH3)2S CH3OH 1.03 2. DMS KMnO4, NaOH cold HI μ Pd or Pt (catalyst) 20 1 19 18 17 16 15 14 13 HBr ROOR (peroxide) H₂O H2SO4 HCI 1. BH3.THF 12 9. 11 10 MCPBA 1. OsO4 2. H₂O₂ CH3CO₂H (peroxyacid) 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF Br- FIOH Pd or Ni (catalyst) D₂ (deuterium) A B 8.8 A B с D 0 H D ४.४
Question 4 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Br2 CH3OH 1.03 2. DMS KMnO4, NaOH cold HI 2. (CH3)2S 18 17 16 15 14 H₂ Pd or Pt (catalyst) 20 1 2 13 12 11 10 MCPBA 1. OsO4 2. H₂O2 CH3CO₂H (peroxyacid) MCPBA A ४.४ A B C D B H₂O HBr ROOR (peroxide) H₂O 8 H2SO4 HCI 1. BH3.THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF Br Pd or Ni (catalyst) D2 (deuterium) EtOH OH OH с OH D OH "OH ४.४ "OH
Question 2 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI MCPBA 1. OsO4 2. H₂O2 CH3CO₂H (peroxyacid) MCPBA 2. (CH3)2S 20 19 18 17 16 15 H₂ Pd or Pt (catalyst) HBr ROOR (peroxide) H₂O H2SO4 HCI 1. BH3⚫THF 2. H₂O2, NaOH 14 Br2 13 12 11 10 H₂O Br2 BH3⚫THF Bra F+OH Pd or Ni (catalyst) D2 (deuterium) A B C D Br Br Br ď ď H "Br "Br 3.8 Α ABCD
Question 19 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. HBr ROOR (peroxide) H₂O Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI mCPBA 1. OsO4 2. H₂O₂ 18 17 16 CH3CO₂H (peroxyacid) 15 14 Pa or Pt (catalyst) 19 20 1 2 13 12 11 10 Pd or Ni (catalyst) D₂ (deuterium) (deuterium) A B H2SO4 HCI 1. BH3⚫THF 2. H₂O2, NaOH Br2 Br2 BH3⚫THF H₂O 0 D OCH3 а Br OCH3 Br OCH3 Br Br OCH3 Br OCH3 Br OCH3 de de de of Br OCH3 OCH3 'Br ABCD
Question 8 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. (CH3)2S Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI Pd or Pt (catalyst) HBr ROOR (peroxide) H₂O 20 1 3 18 4 17 16 H₂SO4 HCI 1. BH3.THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF MCPBA 1. OsO4 2. H₂O2 CH3CO₂H (peroxyacid) MCPBA 15 14 13 9 12 11 10 Pd or Ni (catalyst) D₂ (deuterium) OCH 0 D B ď ď OH Br ОН Br OH 'Br ď ď 'OH Br 'Br OH ce ca OH Br Α ABCD
Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Question 5 2. (CH3)2S Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI MCPBA Pd or Pt (catalyst) HBr ROOR (peroxide) H₂O 20 12 19 18 17 16 15 1. OsO4 2. H₂O2 CH3CO₂H 14 13 (peroxyacid) 12 11 10 H2SO4 HCI 5 1. BH3.THF 6 2. H₂O2, NaOH Br2 Pd or Ni (catalyst) D2 (deuterium) FIOH MCPBA 2. H₂O Br2 H₂O BH3⚫THF A B с D 8.8 A B C 3.8 ४.४
Question 19 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Br2 CH3OH 1.03 2. DMS KMnO4, NaOH cold HI MCPBA 1. OsO4 2. H₂O₂ 19 18 17 16 15 CH3CO₂H (peroxyacid) 14 13 Pd or Pt (catalyst) 20 12 12 11 10 D₂ (deuterium) HBr ROOR (peroxide) H₂O 8 H2SO4 HCI 1. BH3.THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF A B с D OCH3 Br Br OCH3 'Br OCH3 OCH3 Br OCH3 Br Br OCH3 of de det of Br "OCH3 OCH3 ""Br А A B C O D
Question 19 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Br₂ CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI 18 19 20 1 2 17 16 HBr ROOR (peroxide) H₂O H₂SO4 HCI MCPBA 1. Os04 2. H₂O₂ (peroxyacid) 15 14 13 12 11 10 1. BH3.THF 2. H₂O2, NaOH Br2 H₂O BH3.THF Br₂ B D OCH3 Br Br ď ď ď ď Br OCHS OCH Br OCHS Br ४.४ o de de de Br OCHS OCH ABC о D