If you like us, please share us on social media.
The latest UCD Hyperlibrary newsletter is now complete, check it out.

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

Copyright (c) 2006-2014 MindTouch Inc.

This file and accompanying files are licensed under the MindTouch Master Subscription Agreement (MSA).

At any time, you shall not, directly or indirectly: (i) sublicense, resell, rent, lease, distribute, market, commercialize or otherwise transfer rights or usage to: (a) the Software, (b) any modified version or derivative work of the Software created by you or for you, or (c) MindTouch Open Source (which includes all non-supported versions of MindTouch-developed software), for any purpose including timesharing or service bureau purposes; (ii) remove or alter any copyright, trademark or proprietary notice in the Software; (iii) transfer, use or export the Software in violation of any applicable laws or regulations of any government or governmental agency; (iv) use or run on any of your hardware, or have deployed for use, any production version of MindTouch Open Source; (v) use any of the Support Services, Error corrections, Updates or Upgrades, for the MindTouch Open Source software or for any Server for which Support Services are not then purchased as provided hereunder; or (vi) reverse engineer, decompile or modify any encrypted or encoded portion of the Software.

A complete copy of the MSA is available at http://www.mindtouch.com/msa

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.




Last modified
13:32, 25 Jan 2015



Lower Divisional

Creative Commons License Unless otherwise noted, content in the UC Davis ChemWiki is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 3.0 United States License. Permissions beyond the scope of this license may be available at copyright@ucdavis.edu. Questions and concerns can be directed toward Prof. Delmar Larsen (dlarsen@ucdavis.edu), Founder and Director. Terms of Use