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Chapter 14

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Unformatted text preview: Peter Vollhardt University of California at Berkeley I, too, star TigreDe Bue Aire 1952 lta, nos s, te d small…….. Chapter 14 Delocalized Pi Systems Delocalized Re thedoublebond call Trigonal Theπ bond is e rich: -rich: The E attack, attack add) add Thelobe of thep-orbitals: s Pe ndicular t o thesigm rpe a Pe f ram and paralle t o e e l paralle ach othe r. othe Ethe F ne R∙ 2-Propenyl (Allyl) 2-Propenyl H Que stion: What about adding a third p-orbital t hird -orbital adjace to thedoublebond? nt adjace I s the som thing spe re e cial? Or: Is the any spe re re cial activity at the Or: carbons adjace to a doublebond? nt carbons Re placing oneof thehydroge in e newith anothe sp2ns the r sp Re hybridize carbon give a prope d s nylic or allylic syste . m hybridize allylic Allylic position Obse rvations: a. a. b. H 87 kcal m -1: We ol We ak! H 101 kcal m -1 ol L S1 N S 1 re activity of allylic carbon likethat of RsecX, X, N e n though it is prim ve ary! B H B 50 c. H pKa ~ 40: Acidic! Ac...
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