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Topic 4 Part II Summary: "Haloalkanes"

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Chemistry 1027A/B
Mel Usselman

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Key Concepts In Organic Chemistry: Haloalkanes Part II (Usselman Version) -C-LG can undergo an elimination reaction, in addition to the substitution reactions already discussed. In elimination reactions, the Nu: acts as a base (B) and attacks an H instead of attacking C as a nucleophile. Because the H atom and the LG come off C atoms that are adjacent (often labelled α and β), this reaction is called a β elimination. -All species considered earlier as nucleophiles, can also act as bases (the only difference is whether the species attacks a carbon or an H. We classify a group as a nucleophile or base depending on how it reacts, not on what its structure is. -There are two molecular features which act to increase the yield of elimination products at the expense of substitution products: i) a large anion, and ii) a stable alkene as a product. By Zaitsev’s rule, the alkene with the most alkyl groups will form in greater amounts. -The E2 elimination mechanism is similar to the SN me2hanism. Elimination products by an E2 m
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