Chapter 17 Reduction

The oxidation of one molecule is accompanied by the reduction of another. If an oxidation involves the loss of two electrons, a reduction involves the gain of two electrons. The structural changes in the reduction product are often measured by whether hydrogen is gained or if a heteroatom such as oxygen is lost. This chapter reviews important organic reactions that are classified as reductions. Just as an oxidation is a reaction in which two electrons are lost, a reduction is defined as a reaction in which two electrons are gained. Structural changes used to monitor a reduction are the gain of hydrogen atoms or loss of an oxygen atom or another heteroatom. Lithium aluminum hydride is a more powerful reducing agent than sodium borohydride, so it easily reduces ketones and aldehydes.

Defining a Reduction

Hydride Reducing Agents

Reduction of Heteroatom Functional Groups

Catalytic Hydrogenation of Alkenes

Hydrogenation of Alkynes

Hydrogenation of Other Functional Groups

Dissolving Metal Reductions

Zn, Sn, Wolff Kishner and Clemmensen Reductions

Dissolving Metal Reactions

Homogenous Hydrogenation

Pinacol Coupling

Acyloin Condensation