Not practical TABLE 8.2 GUIDELINES FOR DETERMINING THE REGIOCHEMICAL AND STEREOCHEMICAL OUTCOME OF SUBSTITUTION AND ELIMINATION REACTIONS REGIOCHEMICAL OUTCOME STEREOCHEMICAL OUTCOME The nucleophile attacks the a posi- The nucleophile replaces the leaving tion, where the leaving group is group with inversion of configuration, connected. SN1 The nucleophile attacks the carbo-cation, which is where the leaving group was originally connected, unless a carbocation rearrangement takes place. The nucleophile replaces the leaving group with racemization. The Zaitsev product is generally favored over the Hofmann product, unless a sterically hindered base is used, in which case the Hofmann product will be favored. This process is both stereoselective and stereospecific When applicable, a trans disubstituted alkene will be favored over a cis disubstituted alkene. When the (3 position of the substrate has only one proton, the stereoisomers alkene resulting from ant/-periplanar elimination will be obtained (exclusively, in most cases). E1 The Zaitsev product is always favored over the Hofmann product. The process is stereoselective. When applicable, a trans disubstituted alkene will be favored over a cis disubstituted alkene.