1. 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.

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

7. 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.

8. 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.

9. 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.

10. 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.

11. 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.

12. 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.

13. 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.

14. 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.

15. 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.