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Chemistry LibreTexts

Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions

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  • Nucleophilic addition reactions were described in general terms in Chapter 18. In Chapter 19, we take a more detailed look at these reactions as we make a comprehensive study of the chemistry of aldehydes and ketones. Aldehydes and ketones are discussed together because their chemistry is very similar. However, as you work through the chapter, be sure to look for specific instances where the chemistry of these two classes of compounds differs.

    As usual, we begin the chapter with a discussion of nomenclature. This introduction is followed by descriptions of the methods used to prepare aldehydes and ketones in the laboratory. You will notice that a number of these reactions have already appeared in previous units. Note that an important differences between aldehydes and ketones is the resistance of the latter to oxidation.

    A large part of this chapter is concerned with the addition of various nucleophiles to the carbonyl group of aldehydes and ketones. In particular, we discuss the addition of a variety of nitrogen‑containing compounds—alcohols and phosphorus ylides. Many of these reactions are important to chemists concerned primarily with the synthesis of new organic compounds.

    We also describe the Cannizzaro reaction and conjugate addition to αβ‑unsaturated carbonyl compounds. We mention the occurrence of nucleophilic addition reactions in biological systems, and conclude the unit with a look at the use of spectroscopic techniques in the analysis of aldehydes and ketones.