ABSTRACT

This chapter will introduce the reaction of a base with an alkyl halide, with a hydrogen atom that is on the β-carbon relative to a halide leaving group; the β-carbon is sp3 hybridized. Bond polarization makes the β-hydrogen atom slightly acidic, and reaction with the base expels the leaving group with formation of a new π-bond. In other words, the alkyl halide is converted to an alkene. The reaction just described is a classical acid-base reaction, with the β-hydrogen atom of an alkyl halide reacting as a weak acid. With tertiary halides and an aqueous medium, ionization to a carbocation may occur before loss of the leaving group, but the product is also an alkene. These types of reactions are generically known as elimination reactions.