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Organic Chemistry, 6 th edition Paula Yurkanis Bruice Chapter 20 More About Oxidation–Reduction Reactions Brian L. Groh Minnesota State University, Mankato Mankato, MN Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which set of reagents will accomplish the transformation shown below? 20.2 A.H 2, Raney Ni B.NaBH 4, isopropanol C.1. NaBH 4 2. H 2 O D.1. LiAlH 4 2. H 2 O E.All of the above Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which set of reagents will accomplish the transformation shown below? 20.2 A.H 2, Raney Ni B.NaBH 4, isopropanol C.1. NaBH 4 2. H 2 O D.1. LiAlH 4 2. H 2 O E.All of the above Bruice: Organic Chemistry, © 2011 Pearson Education, Inc. All of these reducing agents are sufficiently strong to reduce an aldehyde.
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Which reducing agent will accomplish the reduction shown below? 20.2 A.H 2, Raney Ni B.1. NaBH 4 2. H 2 O C.1. LiAl[OC(CH 3 ) 3 ] 3 H, -78 °C 2. H 2 O D.1. LiAlH 4 2. H 2 O E.H 2, Lindlar’s catalyst Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which reducing agent will accomplish the reduction shown below? 20.2 A.H 2, Raney Ni B.1. NaBH 4 2. H 2 O C.1. LiAl[OC(CH 3 ) 3 ] 3 H, -78 °C 2. H 2 O D.1. LiAlH 4 2. H 2 O E.H 2, Lindlar’s catalyst Use of tri-tert-butoxy- aluminum hydride at low temperature allows addition of only one equivalent of hydride ion. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which oxidizing agent will accomplish the oxidation shown below? 20.4 A.HIO 4 B.H 2 CrO 4 C.Ag 2 O, NH 3 2. H 3 O + D.H 2 O 2, OsO 4 catalyst E.(CH 3 ) 2 S=O, (COCl) 2, (CH 3 CH 2 ) 3 N Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which oxidizing agent will accomplish the oxidation shown below? 20.4 A.HIO 4 B.H 2 CrO 4 C.Ag 2 O, NH 3 2. H 3 O + D.H 2 O 2, OsO 4 catalyst E.(CH 3 ) 2 S=O, (COCl) 2, (CH 3 CH 2 ) 3 N The Swern oxidation is a very mild and general method for the oxidation of primary alcohols to aldehydes. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which reagent(s) will accomplish the transformation shown below? 20.6- 20.8 A.H 2 O 2, OsO 4 catalyst B.HIO 4 C.t-BuOOH, (i-PrOH) 4 Ti, (-)DET D.CF 3 CO 3 H, H 2 O E.H 2 CrO 4 Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which reagent(s) will accomplish the transformation shown below? 20.6- 20.8 A.H 2 O 2, OsO 4 catalyst B.HIO 4 C.t-BuOOH, (i-PrOH) 4 Ti, (-)DET D.CF 3 CO 3 H, H 2 O E.H 2 CrO 4 Though OsO 4 is highly toxic, OsO 4 catalyzed hydroxylations usually proceed in high yield. Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which set of reagents will accomplish the transformation shown below? 20.10 A.a. [1. Hg(OAc) 2, H 2 O 2. NaBH 4 ]; b. HIO 4 ; c. [1. CH 3 Li 2. H 2 O] B.a. [1. Hg(OAc) 2, H 2 O 2. NaBH 4 ]; b. H 2 CrO 4 ; c. [1. CH 3 MgCl 2. H 2 O] C.a. [1. NaBH 4 2. H 2 O]; b. Swern; c. [1. LDA 2. CH 3 Cl 3. H 3 O + ] D.a. CH 3 CO 2 H; b. [1. CH 3 MgCl 2. H 2 O] E.a. CH 3 CO 3 H; b. Br 2, H 2 O; c. [1. Mg 2. CH 3 Cl 3. H 2 O] Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which set of reagents will accomplish the transformation shown below? 20.10 A.a. [1. Hg(OAc) 2, H 2 O 2. NaBH 4 ]; b. HIO 4 ; c. [1. CH 3 Li 2. H 2 O] B.a. [1. Hg(OAc) 2, H 2 O 2. NaBH 4 ]; b. H 2 CrO 4 ; c. [1. CH 3 MgCl 2. H 2 O] C.a. [1. NaBH 4 2. H 2 O]; b. Swern; c. [1. LDA 2. CH 3 Cl 3. H 3 O + ] D.a. CH 3 CO 2 H; b. [1. CH 3 MgCl 2. H 2 O] E.a. CH 3 CO 3 H; b. Br 2, H 2 O; c. [1. Mg 2. CH 3 Cl 3. H 2 O] Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which set of reagents will accomplish the transformation shown below? 20.10 B.a. [1. Hg(OAc) 2, H 2 O 2. NaBH 4 ] b. H 2 CrO 4 c. [1. CH 3 MgCl 2. H 2 O] Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which set of reagents will accomplish the transformation shown below? 20.10 A.a. PCC/CH 2 Cl 2 ; b. NaBH 4, isopropyl alcohol B.a. [1. O 3, -78 °C 2. (CH 3 ) 2 S]; b. NaBH 4, isopropyl alcohol C.a. CH 3 CO 3 H; b. [1. LiAlH 4 2. H 2 O] D.a. HIO 4 ; b. NaBH 4, isopropyl alcohol E.a. [1. O 3, -78 °C 2. (CH 3 ) 2 S]; b. NaBH 4, CeCl 3, ethanol/H 2 O, -15 °C Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which set of reagents will accomplish the transformation shown below? 20.10 A.a. PCC/CH 2 Cl 2 ; b. NaBH 4, isopropyl alcohol B.a. [1. O 3, -78 °C 2. (CH 3 ) 2 S]; b. NaBH 4, isopropyl alcohol C.a. CH 3 CO 3 H; b. [1. LiAlH 4 2. H 2 O] D.a. HIO 4 ; b. NaBH 4, isopropyl alcohol E.a. [1. O 3, -78 °C 2. (CH 3 ) 2 S]; b. NaBH 4, CeCl 3, ethanol/H 2 O, -15 °C Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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Which set of reagents will accomplish the transformation shown below? 20.10 E. a. [1. O 3, -78 °C 2. (CH 3 ) 2 S] b. NaBH 4, CeCl 3, ethanol/H 2 O, -15 °C Bruice: Organic Chemistry, © 2011 Pearson Education, Inc.
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