Table 11-1, p. 368

Figure 11.7: Energy diagrams showing the effects of (a) substrate, (b) nucleophile, (c) leaving group, and (d) solvent on SN2 reaction rates. Substrate and leaving group effects are felt primarily in the transition state. Nucleophile and solvent effects are felt primarily in the reactant ground state. Fig. 11-7, p. 372

Stereochemistry of an SN1 Reaction Figure 11.11: Ion pairs in an SN1 reaction. The leaving group shields one side of the carbocation intermediate from reaction with the nucleophile, thereby leading to some inversion of configuration rather than complete racemization. We don’t observe complete racemization. Instead a mixture of inversion and racemization Fig. 11-11, p. 375

p. 387

E2 Reaction – The alkyl halide Must be Anti Periplanar Figure 11.18: The transition state for the E2 reaction of an alkyl halide with base. Overlap of the developing p orbitals in the transition state requires periplanar geometry of the reactant. Fig. 11-18, p. 388

E2 Reaction – Does Not Racemize p. 388

Figure 11. 20: Dehydrochlorination of menthyl and neomenthyl chlorides Figure 11.20: Dehydrochlorination of menthyl and neomenthyl chlorides. (a) Neomenthyl chloride loses HCl directly from its more stable conformation, but (b) menthyl chloride must first ring-flip before HCl loss can occur. The abbreviation “Et” represents an ethyl group. Fig. 11-20b, p. 390

Figure 11. 22: Elimination reactions of menthyl chloride Figure 11.22: Elimination reactions of menthyl chloride. E2 conditions (strong base in 100% ethanol) lead to 2-menthene through an anti periplanar elimination, whereas E1 conditions (dilute base in 80% aqueous ethanol) lead to a mixture of 2-menthene and 3-menthene. Fig. 11-22, p. 392