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23: Carbonyl Condensation Reactions

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    Learning Objectives

    When you have completed Chapter 23, you should be able to

    • fulfill all of the detailed objectives listed under each individual section.
    • design multi‑step syntheses in which the reactions introduced in this unit are used in conjunction with any of the reactions described in previous units.
    • solve road‑map problems that require a knowledge of carbonyl condensation reactions.
    • define, and use in context, any of the key terms introduced.

    In this chapter, we consider the fourth and final general type of reaction that carbonyl compounds undergo—the carbonyl condensation reaction. Carbonyl condensation reactions take place between two carbonyl‑containing reactants, one of which must possess an alpha‑hydrogen atom. The first step of the reaction involves the removal of an alpha‑hydrogen atom by a base. In the second step, the enolate anion that results from this removal attacks the carbonyl‑carbon of the second reacting molecule. In the final step of the reaction, a proton is transferred to the tetrahedral intermediate formed in the second step, although in some cases the product that results may subsequently be dehydrated.

    23: Carbonyl Condensation Reactions is shared under a CC BY-SA 4.0 license and was authored, remixed, and/or curated by Steven Farmer & Dietmar Kennepohl.

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