ChemWiki: The Dynamic Chemistry E-textbook > Organic Chemistry > Organic Chemistry With a Biological Emphasis > Chapter 16: Oxidation and reduction reactions

Chapter 16: Oxidation and reduction reactions

Section 16.4: Hydrogenation/dehydrogenation reactions of carbonyls, imines, and alcohols

  1. Nicotinamide adenine dinucleotide - a hydride transfer coenzyme
  2. Carbonyl hydrogenation and alcohol dehydrogenation - the general picture
  3. Stereochemistry of carbonyl hydrogenation and alcohol dehydrogenation
  4. Examples of redox reactions involving alcohols, carbonyl groups, and imines

Section 16.5: Hydrogenation of alkenes and dehydrogenation of alkanes

  1. Alkene hydrogenation in fatty acid biosynthesis 
  2. The flavin coenzymes
  3. Alkane dehydrogenation in fatty acid degradation 
  4. More examples of enzymatic alkene hydrogenation

Section 16.6: Additional examples of enzymatic hydride transfer reactions

  1. More reactions involving nicotinamide adenine dinucleotide and flavin
  2. Reactions with coenzymes derived from folic acid

Section 16.7: NAD(P)H, FADH2 and metabolism - a second look

  1. NADH and FADH2 as carriers of hydrides from fuel molecules to water
  2. The source of NADPH for reductive biosynthesis

Section 16.11: Halogenation of organic compounds

  1. Enzymatic halogenation 
  2. Synthetic parallel - halogenation of alkenes in the lab

Section 16.12: Redox reactions involving thiols and disulfides

  1. Disulfide bridges in proteins
  2. The role of disulfides in the pyruvate dehydrogenase reaction

Section 16.13: Redox reactions in the organic synthesis laboratory

  1. Metal hydride reducing agents
  2. Catalytic hydrogenation and the trans fat issue
  3. Reduction of carbonyl carbons to methylene 
  4. Laboratory oxidation reactions

Section 16.P: Problems for Chapter 16


In this chapter, we will examine for the first time in detail those reactions that involve the oxidation and reduction of organic compounds.  We will learn about how organic redox reactions can take two basic forms.  In one type of redox reaction, a hydrogen molecule (in the form of hydride anion plus a proton) is transferred to or from organic compound: these are called hydrogenation and dehydrogenation reactions. 


In biochemical hydrogenation/dehydrogenation reactions, a hydride ion is transferred directly between the organic substrate and one of two specialized coenzymes called nicotinamide adenine dinucleotide and flavin adenine dinucleotide.

In the second general type of organic redox reaction, one or more heteroatoms (usually oxygen) is inserted into or removed from an organic substrate.  These reactions are catalyzed by two broad classes of enzymes that are generally referred to as oxygenases and reductases, respectively.


Oxygenase/reductase reactions  are mechanistically quite different from hydrogenation/dehydrogenation reactions, and often involve enzyme-bound metals and radical (one-electron) chemistry.  We will see several examples of important oxygenase reactions in the central metabolic pathways, but for most of these, detailed mechanistic discussion is outside the scope of this text. Reducatase reactions will be discussed in the next chapter (section 17.3B) on free radical mechanisms.




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