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Chapter15 Conjugated Systems

by: Faiqa Rahman

Chapter15 Conjugated Systems Chem 2325

Marketplace > University of Texas at Dallas > Chemistry > Chem 2325 > Chapter15 Conjugated Systems
Faiqa Rahman

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About this Document

Part 1 of conjugated systems. Basically a little introduction to it.
Organic Chemistry
Dr. Christina Thompson
Class Notes
conjugated systems, allylic, Organic Chemistry, Bonding, sigma, pi
25 ?




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This 7 page Class Notes was uploaded by Faiqa Rahman on Thursday February 11, 2016. The Class Notes belongs to Chem 2325 at University of Texas at Dallas taught by Dr. Christina Thompson in Spring 2016. Since its upload, it has received 25 views. For similar materials see Organic Chemistry in Chemistry at University of Texas at Dallas.


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Date Created: 02/11/16
Chapter  15  -­‐  Conjugated  Systems     Systems  in  conjugation  are  higher  in  energy  and  more  stable  than   systems  not  in  conjugation               • Not  in   • In  conjugation   conjugation     • More  stable     • Less  stable         Molecular  Orbital:       Node:  where  amplitude   +   equals  zero       −           +   −     p-­‐orbital     +   −           σ  bonding:   If  the  two  s-­‐orbitals  are  in  the  same  phase  then  they  are  bonding                                 If  the  two  s-­‐orbitals  are  not  in  the  same  phase  then  they  are  antibonding                       The  phase  must  overlap  for  bonding  to  occur   Anytime  bonding  occurs,  the  number  of  atomic  orbitals  must  equal  to   the  number  of  molecular  orbitals.   Higher  energy=  out  of  phase  and  are  antibonding   Lower  Energy=  in  phase  and  are  bonding   All  electrons  are  on  the  bottom  because  they  are  bonding.     π-­‐π  bonding:         +   +    Constructive  which  means  they  are  bonding  and  the   energy  required  is  low       −   −           +   −   Deconstructive  which  means  that  they  are  not   bonding  and  the  energy  required  is  high.     −   +         You  are  always  looking  for  the  lowest  energy  possible!!               Because  there  are  p  orbital  clouds  on  the       double  bonds,  the  two  double  bonds  (C  and   2   C ) 3  l  make  a  partial  double  bond  here   because  they  are  in  conjugation  and  are     overlapping         Because  of  this,  electron  from  C  can  move  to  C .     1 4 It  is  also  flat!  If  you  were  to  twist  it  like  this:         It  won’t  work  because  you  lose  the  pi  cloud  that   formed.           Example:                                                     π 4       π 3     Four  electrons  in  pi  bond   in  1,3  butadiene       π 2     Electrons  are   π now     1   constrained.       Basic  energy   situation:     Two  alkenes  not   in  conjugation   +   +   +   +     π 1   Lowest  energy       No  nodes   −   −   −   −                           +   +   −   −     Only  one  node   π 2     −   −   +   +                                           Now  there  are   +   −   −   +   two  nodes   π 3               −   +   +   −                         +   −   +   −     Highest  energy   π 4   3  nodes     −   +   −   +                                   The  lowest  energy    is  the  resonance  stabilization  of  the   conjugated  diene.                             Trans  is  more  stable  than  cis  because  the  Hydrogens  are  not  bumping   into  each  other.     Allylic:      sp 2       p  orbitals  can  interact  with      sp 3   unhybridized  p  orbitals  making    sp 2     it  more  stable                                                                         .         +                                   -­‐                        Cation   Radical   Anion       Allylic  anion  goes  on  C  or  C ,  but  not  C  because  it  is  sitting 1  in   3 2 the  middle.  Same  goes  for  radical  and  cation  as  well.        


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