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Organic Chemistry — Practice Set 4

The substitution and elimination chemistry of alkyl halides: SN2 (concerted, backside attack with inversion) and SN1 (stepwise, carbocation, racemisation), E2 (anti-periplanar, Zaitsev) and E1, Hofmann versus Zaitsev orientation, the substrate, nucleophile/base, leaving-group, solvent and temperature factors that decide the pathway, and the key transformations of alkyl halides (Williamson ethers, nitriles, amines, Grignard reagents, Finkelstein and radical halogenation). Mechanisms and structures are shown in inline notation.