ABSTRACT
Oxygen, fluorine, chlorine, bromine, and iodine are more electronegative than carbon, and so organic molecules with those atoms are electrophilic. Metals are less electronegative than carbon, which means that organometallic compounds (those with a metal–carbon bond) are nucleophiles and bases. In this chapter, organomagnesium (Grignard), organolithium, and organocopper (Gilman) reagents are investigated. First, readers are introduced to the synthesis of these compounds and their skeletal structures, which simplifies their actual structure. From there, we will consider the use of these organometallic reagents in organic synthesis, with an emphasis on their use with epoxides. Finally, this chapter introduces carbenes (R2C) and carbenoid (R2CM, M is a metal) reagents, which can be used to synthesize carbenes through addition to alkenes.
