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Organic Chemistry 2230: Chapter 4 Part B and Chapter 5 Part A

by: Amanda Biddlecome

Organic Chemistry 2230: Chapter 4 Part B and Chapter 5 Part A Chemistry 2230

Marketplace > Clemson University > Chemistry 2230 > Organic Chemistry 2230 Chapter 4 Part B and Chapter 5 Part A
Amanda Biddlecome
GPA 4.0

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These notes cover the last part of chapter 4 and the very beginning of chapter 5.
Organic Chemistry 1
Dr. Schroeder
Class Notes
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This 3 page Class Notes was uploaded by Amanda Biddlecome on Friday February 19, 2016. The Class Notes belongs to Chemistry 2230 at Clemson University taught by Dr. Schroeder in Fall 2016. Since its upload, it has received 27 views.

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Date Created: 02/19/16
Organic  Chemistry  2230   Chapter  4  Part  B   February  19,  2016   Amanda  Biddlecome     1)  Stereoisomers  and  Chirality       -­‐mirror  images=enantiomers  with  different  spins     -­‐don’t  mirror  image  and  swap  bonds  from  the  original  because  they  would  be     identical     -­‐downfall  to  Newman  is  that  you  can’t  see  back  carbons     -­‐Sawhorse  Diagram       *carbon  on  bottom=front  carbon       *carbon  on  top=back  carbon       *halfway  between  skeletal  and  Newman  when  looking  at  it       *benefits  are  that  you  can  see  the  carbon  and  nothing  else  changes         from  the  Newman  Projection         -­‐Fischer  Projection       *starts  with  staggered  Newman  Projection,  make  it  eclipsed,  flip  it  up         onto  its  side       *four  wedges  point  at  you,  two  dashes  point  away  from  you     -­‐spins  in  all  projections       *Newman:  find  the  chiral  carbon  and  pick  it  up  to  look  with  the  lowest       priority  behind       *Fischer  Projection:  count  it  with  it  laying  normally  but  make  sure  #4         doesn’t  face  you  and  if  it  is,  flip  the  spin       -­‐chiral  carbons       *anything  not  sp  hybridized,  you  ignore  it       *put  wedges  and  dashes  anywhere  you  want,  as  long  as  they  are         adjacent  to  one  another  (lowest  priority  in  the  back)       *any  structure  with  a  chiral  will  automatically  have  two  possible         structures:  mirror  images       *don’t  put  wedges  and  dashes  inside  a  ring  (give  dash  and  wedge  to         two  things  coming  off  of  the  ring)       2)  Optical  Activity  and  Polarized  Light     -­‐light  is  random  and  in  waves     -­‐polarize  gives  order  to  disorder     -­‐achiral=no  chiral  carbons     -­‐use  clear  glass  of  water  and  shine  a  light  through  it       *light  comes  out  just  as  it  went  in     -­‐use  sugar  water       *light  comes  out  spiraling  because  of  chiral  carbon     -­‐optically  active  means  it  has  chiral  carbons       *compound  that  rotates  polarized  light       *antichiral=not  active     -­‐dextrorotary=rotates  to  the  right  (+)     -­‐levorotary=rotates  to  the  left  (-­‐)       *only  how  it  rotates  light,  but  it’s  different  than  what  we’ve  been         learning  (doesn’t  refer  to  how  structure  is  put  together,  just  what  it         does)     3)  Stereochemistry  and  Chirality     -­‐2  chiral  carbons       *need  two  letters       *can  get  four  different  structures  by  changing  dashes  and  wedges       *Diastereomers=pair  of  molecules  with  more  than  one  chiral  carbon         and  at  least  two  of  them  share  a  spin         *Enantiomers=more  than  one  chiral  carbon  with  at  least  two  with         opposite  spins         *the  number  of  structures=2 ;  n=number  of  chiral  carbons   n   -­‐Tartic  acid       *two  chiral  carbons:  find  the  two  spins,  reflect  them  and  get  mirror         images  and  enantiomers  (two  more  to  go  now  so  set  up  another  pair),         draw  a  new  fischer  projection  with  switched  locations  for           substituents       -­‐Meso  Compounds       *pair  of  compounds  with  internal  symmetry  plane       *enantiomers,  but  more  specific       -­‐just  because  there’s  a  wedge  doesn’t  mean  it’s  a  chiral  carbon     4)  Stereochemistry  and  Pharmaceuticals     -­‐Prozac       *enantiomers:  separating  them  is  very  difficult       *(S)=good  but  metabolizes  quickly,  so  use  a  mixture  of  (R)  and  (S)  to         balance  it  out       -­‐receptors=bonding  sites  for  enzymes       *some  enantiomers  don’t  bind  properly     Chapter  5  Part  A     1)  Alkenes     -­‐double  bonds     -­‐alkanes  with  double  bonds,  change  the  end  from  –ane  to  –ene       *example:  butane  to  butane     -­‐all  double  bonds  end  in  –ene       *put  the  number  in  front  of  parent  to  show  where  the  double  bond  is     -­‐saturated  compound=completely  full       *molecule  that  can’t  accommodate  anymore  hydrogens       *C H n 2n+2     -­‐unsaturated  compound=incomplete       *don’t  have  the  maximum  number  of  hydrogen         *C H n 2n-­‐2       *rings     -­‐degree  of  unsaturation       *tells  how  many  pi  bonds  or  rings  in  a  molecule       *should  have  one  pi  bond  for  every  two  hydrogen  atoms  removed       *take  the  number  of  hydrogen  needed  to  make  it  saturated,           subtracted  the  number  that  is  there,  divide  by  two    


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