Why are Grignard reagents strong bases?

1 Answer
Oct 14, 2016

A Grignard reagent features a carbon that is more or less directly bound to a metal centre......

Explanation:

...and, therefore, the ipso carbon has strong carbanionic character. This makes it (i) a powerful nucleophile, and (ii) a powerful base.

#RCH_2-X + Mg rarr RCH_2^(delta-)""^(delta+)MgX#

Generally, Grignards reagents are deployed in aprotic media. Addition of water or alcohols usually quench the Grignard, i.e.

#RCH_2^(delta-)""^(delta+)MgX + H_2O rarr RCH_3 + Mg(OH)X#

Sometimes this can be useful synthetically to introduce, say, a deuterium label, #D=""^2H# on a hydrocarbyl chain:

#RCH_2^(delta-)""^(delta+)MgX + D_2O rarr RCH_2D + Mg(OD)X#

This would be a much cheaper way of labelling the alkyl chain than buying pre-deuterated material from a supplier. As deuterated solvents go, heavy water is cheap.