If they are used they will act as a base and deprotonate the acidic hydrogen rather than act as a nucleophile and attack the carbonyl. Except for hydrocarbons, ethers, and tertiary amines, almost all … of a wide range of carbonyl groups. They are also highly basic and react even more rapidly. Limitation of Organometallic Reagents. Grignard reagents are strong bases and strong nucleophiles. A Grignard reagent features a carbon that is more or less directly bound to a metal centre..... ...and, therefore, the ipso carbon has strong carbanionic character. This makes it (i) a powerful nucleophile, and (ii) a powerful base. Because of this they cannot be used as nucleophiles on compounds which contain acidic hydrogens. Since they are made from halides, this reaction, which makes an alkane dimer, could interfere with your synthetic plans for the Grignard reagent. As mentioned in the reading, both organolithium and Grignard reagents are good nucleophiles. Complete the acidbase. Thus, the Grignard reagent methylmagnesium bromide (CH 3 MgBr) behaves as if it were equivalent to the methide ion (CH − 3). As discussed above, Grignard and organolithium reagents are powerful bases. They also act as strong bases in the presence of acidic protons such as −CO 2 H, −OH, −SH… with any water present in the system (moisture-sensitive, see Question 2). Grignard reagents are strong nucleophiles and react readily with the electrophilic carbon atom. Grignards can also act as nucleophiles with halides. The Grignard reagent can therefore serve as a nucleophile because of the attraction between the slight negativeness of the carbon atom in the Grignard reagent and the positiveness of the carbon in the carbonyl compound.
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