CHEM 212 Lecture Notes - Lecture 6: Dehydrohalogenation, Deprotonation, Solvolysis
21 Mar 2016
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Preparaion of unsaturated compound to make the double bonds. Lewis base nu / base e1/e2 -> acid/base. Eliminaion: nu -> e+ w/ displacement of lg on adjacent c. Strong bases -> e- rich (-> po h+) Naoch2ch3 + 2ho + 2na -> 2na+ Does not have steric demands bulky bases | eliminaion. E1 2 separate step; bond cleavage lg, then deprotonated by base. E2 one step deprotonaion / bond cleavage. Sn1 /e1 -> need to stabilize change really good at posiive charge. Eliminaion only occur 180 b/w lg-h. Bond forms from b/w 2 new p orbitals. C-h must be coplanar due to hyperconjugaion efect. There would be cases where e1 does not happen. Always v. sn1 proceeds through the same step. E1 no efect, weak base ok. E2 need a strong base (ca-str) Steric interacion small |sub; large|no sub. E1 polar proic; can store anions. E2 polar aproic; does not inhibit the base. E1/e2 best lg stable anion/neutral.
