"The nucleophilic addition reactionis the most common general reaction type for aldehydes and ketones. Many different kinds of products can be prepared by nucleophilic additions. Aldehydes and ketones are reduced by NaBH4 or LiAlH4 to yield primary and secondary alcohols, respectively. Addition of Grignard reagents to aldehydes and ketones also gives alcohols (secondary and tertiary, respectively), and addition of HCN yields cyanohydrins. Primary amines add to carbonyl compounds yielding imines, or Schiff bases, and secondary amines yield enamines. Reaction of an aldehyde or ketone with hydrazine and base gives an alkane (the Wolff–Kishner reaction). Alcohols add to carbonyl groups to yield acetals, which are valuable as protecting groups. Phosphorus ylides add to aldehydes and ketones in the Wittig reaction to give alkenes. α, β-Unsaturated aldehydes and ketones often react with nucleophiles to give the product of conjugate addition, or 1,4 addition. Particularly useful are the conjugate addition of an amine and the conjugate addition of an organic group by reaction with a diorganocopper reagent."
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John McMurry, Organic Chemistry 8th ed. (2012), Ch. 19. Aldehydes and Ketones: Nucleophilic Addition Reactions.
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