Reactions of Carbonyl Compounds with Hydride Donors and Organometallic Reagents

This chapter examines the nucleophilicity of metal–hydrogen and metal–carbon reagents. It states that carbonyl compounds are electrophilic and react with nucleophiles. The nucleophiles involved in the reactions discussed in the previous chapter all had lone pairs and, in each case, the lone pair was the nucleophilic centre. Metal hydrides and organometallic compounds are a different type of nucleophile in which the nucleophilic site is the σ bonding pair of electrons of the M–H or M–C bond (M = metal). The chapter highlights that they are important reagents for reducing carbonyl compounds to alcohols, and synthesizing alcohols with new C–C bonds from carbonyl compounds. The chapter focuses on these reactions of the carbonyl group. It then considers the aspects of designing an organic synthesis, and functional group protection.