Substitution vs. Elimination Predicting the Products

45 When 2-chloro-1,1,2,3,3-pentamethylcyclohexane is treated with sodium hydroxide, neither E2 nor Sn2 products are formed. Explain. 

We mentioned that predicting the products of substitution and elimination reactions requires three discrete steps  

In the previous two sections, we explored the first two steps of this process. In this last section of the chapter, we explore the third and final step. After determining which mechanism(s) operates, the final step is to consider the regiochemical and stereochemical outcomes for each of the expected mechanisms. Table 8.2 provides a summary of guidelines that must be followed when drawing products. Table 8.2 does not contain any new information. All of the information can be found in this chapter and the previous chapter. The table is meant only as a summary of all of the relevant information, so that it is easily accessible in one location. Let s get some practice applying these guidehnes. 

TABLE 8.2 GUIDELINES FOR DETERMINING THE REGIOCHEMICAL AND STEREOCHEMICAL OUTCOME OF SUBSTITUTION AND ELIMINATION REACTIONS 

The nucleophile attacks the a position, where the leaving group is connected. 

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