reactions for orgo - CH 12 isomerization of internal to...

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CH 12 isomerization of internal to external/terminal triple bond with allene intermediate 1) NaNH2 (NH2 has - charge) deprotonates C closest to C with triple bond 2) left with resonance structure. ..negative over deprotonated C makes double bond and then triple bond’s electrons goes on next neighboring C which gives that C a negative charge) 3) negative charge attacks NH3 to protonate that C which gives allene 4) NH2 deprotonates same C again 5) left with another resonance structure. ..negative over deprotonated C makes triple bond and then double bond next to it’s electrons go on neighboring C (negative charge) 6) negative charge attacks NH3 to protonate that C which gives product (unless not ex- ternal triple bond yet. .then keep repeating steps) Addition of HBr/HCl to 1,3-diene 1) H adds to C1 and double bond goes away 2) left with resonance structure with + charge on either C2 or C4. .C2 more stable and yields more 3) Br(-) or Cl(-) attacks + charged C Diels-Alder 1) alkene attacks a cis 1,3-diene to form 6 membered ring CH 13 Birch reduction with benzene 1) Na radical/NH3 attacks any C, then double bond pushes over and then next double bond’s electrons push on next Carbon (negative charge) 2) negative charge attacks EtOH 3) Na radical adds to the 1 electron (negative charge) 4) negative charge attacks EtOH Birch reduction with EWG on benzene
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1) Na radical/NH3 attacks C para to EWG, then double bond pushes over and then next double bonds electrons push on next carbon (negative charge)
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This note was uploaded on 06/14/2008 for the course CHEM 322 taught by Professor Schneider during the Spring '08 term at University of Delaware.

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reactions for orgo - CH 12 isomerization of internal to...

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