Chem 237 coverage MQ #2 to the Final Chap. 8. Nucleophilic Substitution There are no sections that can be ignored, but you can skip the highlight on p. 335  . Table 8.1 is an important summary of transformations. S N 2 reactions are the only method you have for introducing –CN, -N 3 and –SR groups – and for making ethers and esters (see Table 8.1). The three mechanisms (S N 1, S N 2, and S N 1 with rearrangement) are essential knowledge as is Fig. 8.5. You definitely need to know the relative order of leaving groups and relative nucleophilicities, the difference between nucleophilic substitution by anions and solvolysis reactions (the leaving group abilities in Table 8.9 apply best to S N 1, but are similar to the S N 2 order, see lectures for more details on this). Solvent effect on S N reaction are well presented in the text (for example Tables 8.7 and 8.8). Substitution effects (primary vs secondary, backside hindrance, etc) on S N 2 rates (Table 8.2) important. NH
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