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Organic Chemisty II

by: Ansel Ankunding PhD

Organic Chemisty II CHEM 2320

Ansel Ankunding PhD
Utah State University
GPA 3.99


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This 11 page Study Guide was uploaded by Ansel Ankunding PhD on Wednesday October 28, 2015. The Study Guide belongs to CHEM 2320 at Utah State University taught by Staff in Fall. Since its upload, it has received 39 views. For similar materials see /class/230509/chem-2320-utah-state-university in Chemistry and Biochemistry at Utah State University.

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Date Created: 10/28/15
Chapter 20 More about Oxidation Reduction Reactions Learning Objectives 1 Be able to predict products from reductions N Be able to predict products from oxidation of alcohol aldehydes ketones and alkenes 3 Be able to predict products from hydroxylation of alkenes along with the associated stereochemistry 4 Be able to predict products from oxidative cleavage of l2diols alkenes and alkynes 5 Be able to write the general electronpushing arrowpushing mechanisms of ozonlysis and BaeyerVilliger reaction 6 Be able to employ the reactions taught in Chem2310 and Chem2320 for multiple step synthesis and functional group interconversion S ections 201 202 203 204 205 206 207 208 209 2010 20 11 2012 Reduction Reactions Oxidation of Alcohols Oxidation of Aldehydes and Ketones Oxidation of Alkenes with Peroxyacids Designig a Synthesis VII Controlling Stereochemistry Hydroxylation of Alkenes Oxidative Cleavage of l2Diols Oxidative Cleavage of Alkenes Oxidative Cleavage of Alkynes Designing a Synthesis VII Functional Group Interconversion Biological OxidationReduction Reaction Oxidation of Hydroquinones and Reduction of Quinones Sections that will be focused Sections that will be skipped Recommended additional problems 2034 7 2042 2044 7 2053 2060 7 2065 Class Note 201 Reduction Reactions A H2 Pd Pt or Ni M gt H2 i Pd Pt or Ni gt B H2 PdC quinoline gt V Lindlar catalyst C H2 W Raney Ni gt 0 H2 WH Raney Ni gt O D Lindlar W0 catalyst gt O E Na or Li NH3 qu G 1 NaBH4 W 2 H3O O 1 NaBH4 WH 2 H30 O 1 NaBH4 00112013 2 H3O V O 1 NaBH4 NHCH20H3 2 H3O W O H 1 LiAH4 2 H3O gt O H 1 LiAIH4 2 H3O gt O 1 LiAIH4 OCH20H3 2 H3Oquot V O 1 LiAIH4 NHCHZCH3 2 H3O W O H2 Raney Ni 202 Oxidation of Alcohols and 203 Oxidation of Aldehydes and Ketones CrO3 H2804 gt WOH Na20r207 WOH st04 gt H2004 gt CrO3 H2804 gt O Na20r207 H2804 D Swern oxidation 00002 CH3SOCH3 DMSO WOH E BaeyerVilliger oxidation 0 O RCO3H gt CH20H3 O RCOgH gt CH20H3 ii Mechanism iii Relative migration tendency H gt 30 alkyl gt 20 alkyl gt 10 alkyl gt methyl 204 Oxidation of Alkenes with Peroxyacids A R RCO3H gt B Mechanism 206 Hydroxylation of Alkenes and 207 Oxidative Cleavage of 12Diols 1 0804 H202 2 H20 208 Oxidative Cleavage of Alkenes A Ozonolysis 1 O3 78 C 2 workup B Mechanism of the rst step C Examples 0 1 o3 78 C 2 Zn gt 1 o3 78 C 2 H202 ii iii 1 o 78 c 2 C3H3bs gt 1 o3 78 C 2 H202 gt 2010 Designing a Synthesis VII Functional Group Interconversi0n A synthes1s from B H synthesis from


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