CHE 331.800 12.5

CHE 331.800 12.5 - CH 6 551'800 Lg Levra O Radical Addition...

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Unformatted text preview: CH 6 551'800 Lg Levra O Radical Addition to Alkenes: The anti- Markovnikov Addition of Hydrogen Bromide I} Addition of hydrogen bromide in the presence of peroxides gives anti-Markovnikov addition. ROOR CH3CH=CH2 + Hllr -—> CH3CH2CHZBr l-Bromopropane CH3CH=CH2 + HBr CHICHCH3 Murkovnikov addition peranch ‘ I Br 2-Bromopropnnc Mechanism: Chapter [0 3 l Anti-Markovnikov addition e’w/tfi/fil 11/24/14 OR adical Polymerization of Alkenes: Chain-Growth Polymers I} Polymers are macromolecules made up of repeating monomer subunits. It Polyethylene is made of repeating subunits derived from ethylene t,{,’\lnnumrric ll!11t.‘~\_\ / \ l v > ' ,- l' I V t m CH3=CHZ CHZCHZ cnzcnz—hCHZCHz— Ethylene Polyethylene monomer polymer (In and u are large numbers) I} Polystyrene is made in an analogous reaction using styrene as the monomer. m CH2=CH 'wly'm‘m‘m‘” (:ch +CH2CH a; midi— Styrene Polystyrene 32 ofiartheaifiYg monOn/mb mils ' Poiljstgmum M5 a Vir’lfg inéfilflé/ [g H. 16 11/24/14 fl A very small amount of diacyl peroxide ls added in initiating the reaction so that few but very long polymer chains are obtained Chain Initiation 0 II A Step] R~C~O:O— U Diacyl pegoxide SrmZ R-+CHw—k——CH,——+R=C, I Vv _ 1 0 ll 'l‘ht- diacyl permith dissociates unit releases curlmn ilimitlc gas. Aliql radicals are pmducuL which in mm initiate i‘llztillS. I) The propagation step simply adds more ethylene molecules to a growing chain Chain Propagation Step 3 R—CHZCHZ —> R+CHJCH3—)I-ICH_,CH,- Chains propagate by adding: Sucrcwiw ethylene units, until their growth is stopped by mmhirmtion or dis’pi‘nportiimention. Chapter It) 33 I9 Chain branching occurs by abstraction of a hydrogen atom on the same chain and continuation of growth from the main chain. Chain Branching //"\ K ("H, H”) I R—CHICH CHz —> RCHIQH+CH:(IHJ—&;CH3CH‘.—H \l‘ClLClLf ' ' it‘ll; » (in, RCHICHv+CHJCH21CH3CH3 (‘l [1 1 CH, late cnmhinution Chain Termination [R-(-CH2Cl-{1 figCHzCJlI-jg Step 4 2 R-(—CHZCHZ-thHZCI-l2 - disproportiomtion R+CHZCH,3—t;CH=CH._, R+CH2CH3—);CH2CH3 The radical at the cm! of the growing polymer chain can also abstract at ludmgen mom from itselfby Mint is called "back biting,“'1“his limits to chain branching. 17 11/24/14 Examples of Polymers "w Monofler _ w Polymer mm _ M Names_7___ m CH2=CHCH4J +CH2—CH a; Polypropylene 3mg CHZ=CHC| —( CHP—CH an- Poly(viny| chloride). PVC c‘. CH2:CHCN “6 Clix—CH“); Polyacrylonltrile. Orlon (EN OFT-=CF2 -(—CF2— CF2—)7, Polytelrafluoroethene. Teflon CH3 CH3 CH2——=([3C020H3 '*( CHz—(l3 )5 Poly(methy| methacrylate). (IZOECHB Lucite. Plexiglas. Perspex Chapter [0 35 Calicheamicin y,‘ Chapler 10 36 20000 a 1+ " 'fi“ 317 \ W‘DHOQ 1/ 18 11/24/14 Bergman I!) nuclmphilic cyclo— almck H011”, V are mutizalion -———-—-—> —> (3) conjugate addi lion Calichcamicin y.‘ DNA dirudicul 03 DNA double strand cleavage 19 m : ,Wsmm 2? jXKBfiUCUM%— , a S, floMf . W/ 3 Rm; 6 $$_-_ ELDCQJE mafia W'ébonfibnéfif ...
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