Question 2Please 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.Br2CH₂OH1.032. DMSKMnO4, NaOHcoldHIMCPBA1. OsO42. H₂O2CH3CO₂H(peroxyacid)MCPBA2. (CH3)2S201918171615H₂Pd or Pt (catalyst)HBrROOR (peroxide)H₂OH2SO4HCI1. BH3⚫THF2. H₂O2, NaOH14Br2131211 10H₂OBr2BH3⚫THFBraF+OHPd or Ni (catalyst)D2 (deuterium)ABCDBrBrBrď ďH"Br"Br3.8ΑABCD

Addition of HBr to alkene occurs via addition of H+ first followed by addition of Br-. The…

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. 1.03 2. DMS Br2 CH₂OH KMnO4, NaOH cold HI MCPBA 1. OsO4 2. H₂O₂ CH,COSH (peroxyacid) 1. MCPBA 1. 03 2. (CH3)2S ZH HBr Pd or Pt (catalyst) 19 20 1 2 106 45 HBr ROOR (peroxide) H₂O H₂SO4 HCI 1. BH3.THF 2. H2O2, NaOH Br2 18 17 16 655 15 2. H₂O* 14 12 11 10 6 Br₂ H₂O BH3⚫THF Br2 Pd or Ni (catalyst) D₂ (deuterium) EtOH A B H Br Br H 'Br с D Br میں ملی H "Br

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. 1.03 2. DMS Br2 CH₂OH KMnO4, NaOH cold HI MCPBA 1. OsO4 2. H₂O₂ CH,COSH (peroxyacid) 1. MCPBA 1. 03 2. (CH3)2S ZH HBr Pd or Pt (catalyst) 19 20 1 2 106 45 HBr ROOR (peroxide) H₂O H₂SO4 HCI 1. BH3.THF 2. H2O2, NaOH Br2 18 17 16 655 15 2. H₂O* 14 12 11 10 6 Br₂ H₂O BH3⚫THF Br2 Pd or Ni (catalyst) D₂ (deuterium) EtOH A B H Br Br H 'Br с D Br میں ملی H "Br

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter10: Oxidation And Reduction

Section: Chapter Questions

Problem 4CTQ

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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 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
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 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 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
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 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 9 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) 20 18 17 16 15 14 13 Pd or Pt (catalyst) 1 4' 9 12 11 10 Pd or Ni (catalyst) (deuterium) O HBr ROOR (peroxide) H₂O H2SO4 HCI 1. BH3.THF 2. H₂O2, NaOH Br2 H₂O BH3⚫THF Br2 A B 0 D H BH2 H BH2 ***BH₂ BH2 ď ď ď ď BH2 H ***BH₂ Α ABCD
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 6 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. 2. (CH3)2S Br2 CH3OH 1.03 2. DMS KMnO4, NaOH cold HI 12 Pd or Pt (catalyst) HBr 20 1 2 18 17 16 15 HBr ROOR (peroxide) H₂O H2SO4 HCI 1. BH3⚫THF 6 2. H₂O2, NaOH Br2 8. 12 11 10 Br2 14 13 MCPBA 1. OsO4 2. H₂O2 CH3CO₂H (peroxyacid) EtOH deuterium) Pd or Ni (catalyst) A B H₂O BH3⚫THF 0 D H OH ** OH OH ď ď OH H OH ہی ہے OH H OH ď ď 'OH Α A B C D
Q3- Draw the product and write the reagents of the following reactions. When a racemic mixture is formed, you must draw hoth enantiomers and write "racemie" in the box Bra, hv NaCN, DMF Br t-BUOK, t-BUOH NANH, Br NAOCH, CH;NH2 CH,OH Br NaN, NaOCH CH,OH t-BUOK, t-BUOH