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Understanding Oxidation-Reduction Reactions in Organic Chemistry - CWRU Perspective, Essays (university) of Chemistry

This chapter from 'Organic Chemistry' by Paula Yurkanis Bruice explores various aspects of oxidation-reduction reactions. Topics include understanding oxidation and reduction, identifying reducing and oxidizing agents, and discussing different methods for oxidizing and reducing organic compounds. Real-life examples using hydrogen, sodium borohydride, hydrazine, bromine, and chromic acid are provided. The chapter also covers the oxidation of alcohols, aldehydes, ketones, and alkenes, as well as the role of biological oxidation-reduction reactions in organic chemistry.

Typology: Essays (university)

2020/2021

Uploaded on 07/12/2021

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Organic Chemistry
4th Edition
Paula Yurkanis Bruice
Chapter 20
More About
Oxidation–Reduction
Reactions
Irene Lee
Case Western Reserve
University
Cleveland, OH
©2004, Prentice Hall
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Organic Chemistry 4 th Edition Paula Yurkanis Bruice

Chapter 20

More About Oxidation–Reduction Reactions Irene Lee Case Western Reserve University Cleveland, OH

  • (^) Oxidation is always coupled with reduction
  • (^) Loss of electrons is oxidation
  • (^) Gain of electrons is reduction
  • (^) The oxidation state of a carbon atom equals the total number of its C–O, C–N, and C–X bonds

Hydrogen, sodium borohydride, and hydrazine are the reducing agents

Bromine and chromic acid are the oxidizing agents

Reduction by Catalytic Hydrogenation

Dissolving-Metal Reduction

LiAlH 4 is a stronger reducing agent than NaBH 4 LiAlH 4 is used to reduce compounds that are nonreactive toward NaBH 4

DIBAL allows the addition of one equivalent of hydride to an ester Replacing some of hydrogens of LiAlH 4 with OR groups decreases the reactivity of the metal hydride

NaBH 4 can be used to selectively reduce an aldehyde or a keto group in a compound

Oxidation of Alcohols

Mechanism of Alcohol Oxidation by

Chromic Acid

The oxidation of a primary alcohol can be stopped at the aldehyde if pyridinium chlorochromate (PCC) is used as the oxidizing agent