ABSTRACT
If a nucleophile reacts with a ketone or aldehyde to give a good yield of the alkoxide product, hydrolysis leads to an alcohol product, as shown in Figure 18.1. Any nucleophile that gives the alkoxide product directly and essentially irreversibly is considered to be a strong nucleophile. In other words, a practical denition of a strong nucleophile is one that reacts with an aldehyde or ketone to give a good yield of an acyl addition product, and the reaction should be largely irreversible. Common strong nucleophiles include carbon nucleophiles (e.g., the cyanide ion, alkyne anions, and Grignard reagents, introduced in Sections 15.1 through 15.4). In addition, organolithium reagents that were introduced in Chapter 15 are strong nucleophiles. e following Sections discuss acyl addition reactions with strong nucleophiles.
