Chapter 13. Chemical Transformations I: Hydrolysis and Reactions Involving Other Nucleophilic Species

Summary

Due to the uneven electron distributions between atoms in organic compounds such as organohalides and esters, the polar bonds may be the site of chemical reactions in which a nucleophilic species is attracted to the electron-deficient atom of the bond. The molecular scale view of this bond-making and breaking is described, and concepts to understand the dependencies on electronic, steric, and resonance effects are discussed. A special case, called elimination, is described in which the attack initially occurs at an adjacent carbon atom, resulting in deprotonation and allowing double bonds to be formed. Models are developed allowing the relative rates of reactions to be understood as functions of (a) the nucleophile, (b) neighboring group effects on the electron-deficiency and the point of attack, and (c) the ease with which the leaving group separates from the initial organic compound.