ࡱ> 574x_ TFbjbj Wbb+%***>>>8vTt>(>$'''''''$)5,'Q*"'$E(28*$''N&|6'$&'[(0(&Z,,$6',*6'0")E_''n(, : Properties of Carbanions/organometallic compounds: M-R I. measurement of strong bases large pKa of conjugate acid weak acids a. equilibrium dissociation related to basic solution b. basicity function: -  EMBED Equation.3  where H- equivalent to pH. c. function is measured with indicators solution H-1 M KOH14.010 M KOH17.01.0 M NaOMe in MeOH17.00.01 M NaOEt in 20:1 DMSO-EtOH21.0 d. Need different method for really weak bases e. reduction potential of radical reduction and bond energies:  EMBED Equation.3  RHpK(DMF)Methane48Ethane51Propene38diphenylmethane31 II. unless highly stabilized, most carbanions are polar covalent ionic for low electronegativities of M, approximate carbanions III. aggregation is common a. lithium reagent usually form clusters b. 2RMgX ( R2Mg + MgX2 ( R2MgSYMBOL 183 \f "Symbol"MgX2 solvent and R affects equilibrium, halide used affects dimer and cluster formation IV. metals coordinate lone pairs of solvent Generation of carbanions (see March Chapter 12) I. metallodehalogenation: EMBED Equation  EMBED Equation  EMBED Equation  EMBED Equation  II. Metallation: EMBED Equation  a. acid-base reaction b. R'M is often butyl lithium, LDA (lithium diisopropyl amide), could be KOH for stronger acids c. RH must be stronger acid but kinetics may not always be favorable d.  EMBED Equation.3  why is this favorable? III. transmetallation with zero valent metal: EMBED Equation  forward reaction favored when M more electronegative than M'  EMBED Equation.2  IV. transmetallation with a metal halide, EMBED Equation  forward reaction favored when M' is more electronegative than M  EMBED Equation.2  V. transmetallation with other organometallic compound EMBED Equation  general rule: strongest acid pairs with strongest base (most electronegative acid pairs with most electropositive base) VI. EMBED Equation  rare because of competition from Wurtz reaction, elimination Reactivity/reactions of carbanions I. reactivity of carbanion usually estimated from pKa of conjugate acid a. also use equilibrium RLi + R'I ( RI + R'Li vinyl < phenyl < cyclopropyl < ethyl < n-propyl < isobutyl < neopentyl < cylcopentyl b. or R2Mg + R'2Hg ( R2Hg + R'2Mg phenyl < vinyl < cyclopropyl < methyl < ethyl < isopropyl c measure of relative affinity for Li and I, Mg and Hg II. gas-phase measurements give different results III. stabilization by delocalization, ewg, s character, dipole a-stabilization NO2 > COR > COOR > SO2R > CN SYMBOL 187 \f "Symbol" CONH2 > X > H > R IV. carbanion reactivity depends on metal counter ion Rates: Li+ < Na+ < K+ V. unconjugated carbanions are probably sp3 (a) can be formed at bridgeheads (unlike carbocations) (b) invert rapidly  VI. vinyl anions retain stereochemistry Reactions and Mechanisms React with electrophiles: acid, SN2, displacement of leaving group, polar multiple bonds I. DEAE (SE2) front side and backside attack  EMBED ChemWindow.Document  II. cyclo-DEAEDnAn (SEi)  EMBED ChemWindow.Document  most bimolecular substitutions occur with retention of configuration requiring front side attack and it is difficult to distinguish mechanisms III. DE + AE (SE1) EMBED Equation  A. racemization, inversion or retention can occur depending on solvent and carbon anion formed IV. Structure/Reactivity A. SE2 backside attack slows with a branching B. mechanism is usually SE2 or SEi for electronegative metal (Hg, Cd, Zn, Si), and SE1 for electropositive groups (K, Na, Ca) C. kinetic and thermodynamic control  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  Selected reactions I. NH2- can exchange alkane CH by SE1 II. base catalyzed enolization of carbonyls EMBED MSDraw \* mergeformat 7hi) T ]        . / _ ` b c d . ð꣖࣌}j꣖`hgBCJOJQJ%j8hhCJEHOJQJUjn6O hUVnHtHhCJOJQJhhz3ACJOJQJhhCJOJQJ%jhhCJEHOJQJUj%l6O hUVnHtHjhCJOJQJUhqOCJOJQJhCJOJQJh5CJOJQJ 7 ) 3 6 7 ? 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