Question 7 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 A O A B C 20 1 2 19 18 17 16 15 HBr ROOR (peroxide) H₂O 9 12 11 10 mCPBA 1. OsO4 2. H₂O₂ CH3CO₂H (peroxyacid) 14 13 Br D EtOH D₂ (deuterium) Pd or l B с Br Br Br Br Br Br 3.8 H₂SO4 HCI 1. BH3.THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF D Br Br 'Br Br Br Br Br Br

Question 7 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 A O A B C 20 1 2 19 18 17 16 15 HBr ROOR (peroxide) H₂O 9 12 11 10 mCPBA 1. OsO4 2. H₂O₂ CH3CO₂H (peroxyacid) 14 13 Br D EtOH D₂ (deuterium) Pd or l B с Br Br Br Br Br Br 3.8 H₂SO4 HCI 1. BH3.THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF D Br Br 'Br Br Br Br Br Br

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter5: Stereochemistry At Tetrahedral Centers

Section5.SE: Something Extra

Problem 77AP

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ABCD 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. Br₂ CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI MCPBA 1. Os04 2. H₂O₂ CHCO H 20 18 17 16 15 (peroxyacid) B Pd or Pt HBr ROOR (peroxide) H₂O H₂SO4 HCI 14 13 12 11 10 3 1. BH, THF 2. H₂O₂, NaOH Br₂ Br2 H₂O BH3⚫THF D OH OH OH OH OH OH OH "OH OH OH OH фон OH OH OH OH 'OH OH OH "OH
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 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 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 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 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
Please fill in the missing reactants, reagents or products in the following reactions. Indicate relative stereochemistry where it is necessary CI j)
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 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
Kelerences Keview topic Draw a structural formula for the major product of the reaction shown. Cl2 H20 CH;CH2CH;CH=CHz • Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. Do not show stereochemistry in other cases. • If the reaction produces a racemic mixture, just draw one stereoisomer. 2reg 2reg M) ots 2reg pts 2req 1 pts 2req 1 pts 2reg ...1 pts ChemDoodle Previous Next> Save and Exit APR tv MacBook Air 80 DII DD F3 F4 FS F6 F7 F8 F10 F1 F12 #3 $ & + 3 4 6. 7 8 %3D dele E Y | { } P [ F G H. J K C V N M ? .. .. * C0 B
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
b) DRAW THE product of each of the following reactions? DRAW expected product stereochemistry, where NEEDED TO b) חוו H3C- Pd(OAc)2 Ag2CO3 dppe H OBn 1. B2H6, THF CH3 CH3 2. NaOH, H2O2 B 0