5. The mechanism below has 3 errors in it. The possible errors include arrows (wrong direction, type, placement, etc.) and incorrect charges. There is no guarantee that each type of error has been made. Circle each error. 3 points ago. ago. :C1: 6. Each synthesis below has two proposed routes. Circle the preferred route in each case. 4 points OH 1) TsCI, pyridine 2) NaCN, DMSO 1) 03 2) Me₂S 3) PCC CN (rac) (rac) 1) SOCl2, pyridine 2) NaCN, DMSO 1) H2, Lindlar's cat. 2) MCPBA 3) NaOH OH OH (rac) 1) Na, NH3 (liq.) 2) OsO4, H₂O 1) BH3 2) NaOH, H2O2, H₂O 3) K2Cr2O7, H2SO4 1) Br2, light 2) EtONa, EtOH 3) CH2l2, Et2Zn 1) Cl2, light 2) NaOtBu, DMSO 3) CHCl3, NaOtBu OH

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 5E
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5. The mechanism below has 3 errors in it. The possible errors include arrows (wrong direction, type,
placement, etc.) and incorrect charges. There is no guarantee that each type of error has been
made. Circle each error. 3 points
ago. ago.
:C1:
6. Each synthesis below has two proposed routes. Circle the preferred route in each case. 4 points
OH
1) TsCI, pyridine
2) NaCN, DMSO
1) 03
2) Me₂S
3) PCC
CN
(rac)
(rac)
1) SOCl2, pyridine
2) NaCN, DMSO
1) H2, Lindlar's cat.
2) MCPBA
3) NaOH
OH
OH
(rac)
1) Na, NH3 (liq.)
2) OsO4, H₂O
1) BH3
2) NaOH, H2O2, H₂O
3) K2Cr2O7, H2SO4
1) Br2, light
2) EtONa, EtOH
3) CH2l2, Et2Zn
1) Cl2, light
2) NaOtBu, DMSO
3) CHCl3, NaOtBu
OH
Transcribed Image Text:5. The mechanism below has 3 errors in it. The possible errors include arrows (wrong direction, type, placement, etc.) and incorrect charges. There is no guarantee that each type of error has been made. Circle each error. 3 points ago. ago. :C1: 6. Each synthesis below has two proposed routes. Circle the preferred route in each case. 4 points OH 1) TsCI, pyridine 2) NaCN, DMSO 1) 03 2) Me₂S 3) PCC CN (rac) (rac) 1) SOCl2, pyridine 2) NaCN, DMSO 1) H2, Lindlar's cat. 2) MCPBA 3) NaOH OH OH (rac) 1) Na, NH3 (liq.) 2) OsO4, H₂O 1) BH3 2) NaOH, H2O2, H₂O 3) K2Cr2O7, H2SO4 1) Br2, light 2) EtONa, EtOH 3) CH2l2, Et2Zn 1) Cl2, light 2) NaOtBu, DMSO 3) CHCl3, NaOtBu OH
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