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Organic Chemistry 2230: Chapter 3 Part B and Chapter 4 Part A notes

by: Amanda Biddlecome

Organic Chemistry 2230: Chapter 3 Part B and Chapter 4 Part A notes Chemistry 2230

Marketplace > Clemson University > Chemistry 2230 > Organic Chemistry 2230 Chapter 3 Part B and Chapter 4 Part A notes
Amanda Biddlecome
GPA 4.0

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About this Document

These notes cover the tail end of Chapter 3 and the beginning of Chapter 4.
Organic Chemistry 1
Dr. Schroeder
Class Notes
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This 3 page Class Notes was uploaded by Amanda Biddlecome on Friday February 12, 2016. The Class Notes belongs to Chemistry 2230 at Clemson University taught by Dr. Schroeder in Fall 2016. Since its upload, it has received 21 views.


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Date Created: 02/12/16
Organic  Chemistry  2230   Chapter  3:  An  Introduction  to  Organic  Compounds   February  8,  2016   Amanda  Biddlecome     1)  Conformations  of  Alkanes     -­‐representations  of  structures       *skeleton  is  what  we  see  the  most  often       *want  to  be  able  to  go  from  3D-­‐2D  on  paper  so  just  change  the           perspective  you  look  at  it  from       *Newman  Projection       *staggered  structure=stable;  the  bonds  offset  each  other       *eclipsed  structure=not  stable;  when  atoms  line  up  directly  behind         one  another     -­‐staggered  is  more  stable  because  the  hydrogen  atoms  have  as  much  space     between  them  as  possible       2)  Conformations  of  n-­‐butane     -­‐n=because  there’s  3  other  possible  but-­‐  groups     -­‐either  staggered  or  eclipsed  when  looking  down  the  bond  from  Carbon  1  to     Carbon  2     -­‐when  you  look  down  the  bond  between  Carbon  2  and  3  is  when  you  get  a     switch  up  and  can  have  different  versions  of  the  eclipsed  structure       *each  possible  structure  has  different  potential  energy       *the  most  stable  staggered  is  when  the  two  extra  carbons  are  opposite       one  another-­‐called  Anti-­‐(the  big  group  on  the  front  is  anti  to  the  big         group  on  the  back)     3)  Conformations  of  Cyclohexane     -­‐hexagon     -­‐we  take  it  (the  ring)  and  then  lay  it  down  flat  when  we  draw  it     -­‐2D=chair  conformation       *not  easy  to  draw       *series  of  3  parallel  lines       *start  at  top  right  corner  and  vertical  bonds  alternate  up  and  down         (up  bond=axial  up;  down  bond=axial  down)       *other  bonds  go  at  angles  to  the  molecule  (equatorial  up  and           equatorial  down)       *you  can  switch  the  confirmation  by  taking  the  “1”  corner  and           bending  it  down  and  the  “4”  corner  and  bending  it  up-­‐named  a  ring         flip  and  is  basically  the  same  that  you  do  to  switch  between  staggered         and  eclipsed  (axial  becomes  equatorial  and  equatorial  becomes  axial)       *when  groups  are  in  equatorial  position,  they  are  more  stable  than         when  they  are  in  axial  position     4)  Monosubstituted  Cyclohexanes     -­‐methyl  group  and  cyclohexanes     -­‐can  make  it  so  methyl  is  in  equatorial  position     -­‐do  a  ring  flip  and  it  becomes  axial     -­‐methyl  group  points  down  in  both,  but  position  changes     -­‐equatorial  position  is  more  stable       *the  thing  bonded  to  cyclohexane  should  be  in  this  position     5)  Disubstituted  Cyclohexanes     -­‐2  things  bonded  to  cyclohexane       *2  positions  have  the  same  name,  but  are  different     -­‐prefixes       *cis=same  side  (both  pointing  the  same  way:  down  or  up)       *trans=opposite  side  (they  are  pointing  in  opposite  directions)       *only  works  with  two  substituents       *cis  ring  flip=both  still  pointing  in  the  same  direction,  they    just  switch       positions       *trans  ring  flip=both  still  pointing  opposite  directions  but  now  they         both  have  the  opposite  position       *when  looking  at  structures,  a  wedge  bond  means  it’s  pointing  at  you,         and  a  dash  bond  means  it’s  pointing  away  from  you       *wedge  becomes  up  bond,  and  dash  becomes  down  bond  when  you         flip  it     -­‐stability       *equatorial=more  stable       *bigger  groups  on  equatorial  position=more  stable     Chapter  4:  Stereochemistry     1)  Isomers     -­‐Constitutional=same  formula,  different  structure  to  represent  it     -­‐Functional  group       *ether  vs.  alcohol       *same  formula,  but  different  possible  parents     -­‐3D:  trans  vs.  cis  with  the  same  formula  and  structure     -­‐ring  flips     -­‐Chiral  Carbon=4  diffe3ent  things  bonded  to  a  carbon       *sp  hybridized       *any  carbon  with  a  double  or  a  triple  bond  can’t  be  this       *mirror  images     -­‐Enantiomers=structures  are  different  because  if  you  lay  them  across  each     other,  all  portions  will  never  overlap       *non-­‐superimposable  mirror  images       *in  pharmaceuticals,  you  can  get  two  different  drugs  through  mirror         images  because  they  target  different  receptors   2)  Stereoisomers  and  Chirality     -­‐tripod=template  to  help  convert  between  mirror  images     -­‐naming  (another  naming  system)       *1)  Identify  the  four  things  that  are  bonded  to  the  chiral  carbon  and         prioritize  them  by  atomic  number  (look  at  the  individual  atoms;  when       there’s  two  of  the  same  atom  attached  to  the  chiral  carbon,  look  at  the         longer  chain  to  determine  which  has  the  larger  atomic  number)       *2)  draw  an  arrow  from  the  highest  priority  (first)  to  the  lowest  (last)       *3)  clockwise  circle=R-­‐  as  a  prefix;  counterclockwise  circle=S-­‐  as  a         prefix  (the  letter  will  always  come  at  the  very  beginning  of  the  name)       *before  assigning  the  letter,  make  sure  the  lowest  priority  group  faces         away  from  you  (look  at  the  model  from  the  bottom  of  it  so  the  front         half  looks  like  a  Newman  Projection)  


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