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Organic Chemistry: Week One Notes

by: Amanda Biddlecome

Organic Chemistry: Week One Notes CH 2240

Marketplace > Clemson University > Chemistry > CH 2240 > Organic Chemistry Week One Notes
Amanda Biddlecome
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About this Document

These notes are from Chapter 14 and week 1.
Organic Chemistry
Dr Schroeder
Class Notes




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This 4 page Class Notes was uploaded by Amanda Biddlecome on Sunday August 28, 2016. The Class Notes belongs to CH 2240 at Clemson University taught by Dr Schroeder in Fall 2016. Since its upload, it has received 38 views. For similar materials see Organic Chemistry in Chemistry at Clemson University.


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Date Created: 08/28/16
Organic  Chemistry  2240   August  17,  2016   Amanda  Biddlecome   Chapter  14:  Mass  Spectrometry  and  Infrared  Spectrometry     1)  Addition  Reactions     -­‐more  substituted  halide  is  the  major  product  because  the  cation  forms  there       *regiospecific     -­‐add  hydrogen  peroxide  to  get  the  minor  as  prominent  product     -­‐3  questions       *What  forms?       *Where  does  it  form?       *How  does  it  form?     2)  Radical  Reactions     -­‐What  happened  to  go  in  the  anti  direction?     -­‐hydrogen  peroxide  breaks  and  you  have  single  hook  arrows  indicating  that     one  electron  goes  to  each  side     -­‐compounds  with  unpaired  electrons  are  radicals/oxidents  and  are  very     reactive     -­‐HX  breaks  apart  like  how  the  O-­‐O  bond  breaks       *products  are  hydrogen  peroxide  and  X  radical  and  is  still  reactive   o     *break  the  double  bond  between  the  carbons  and  electron  goes  to  3         carbon  that  forms  a  bond  with  H  and  X  goes  to  the  terminal  carbon     -­‐anytime  you  see  hν     3)  Addition  Reactions     -­‐tertiary  carbocation  is  the  most  stable       *Markovnikov  Rule     -­‐Radical  Halogenation  Reactions       *forms  alkyl  halides       *forms  on  the  most  substituted  carbon       *stereochemistry  is  racemic     4)  Identification  of  Compounds     -­‐mass  spectrometer  forms  radicals  and  cations       *measures  molecular  mass  and  finds  the  formula       *how?-­‐sample  in  solution  goes  in  and  goes  through  electron  beam  and       goes  through  a  tube  with  magnets  and  fragments  are  analyzed  by  the         cations  and  radicals  that  are  produced  (we  see  the  cations  and  use         math  to  get  the  radicals)       *tells  the  mass  and  abundance  of  particles  formed         ^abundance  corresponds  to  stability       *molecular  ion  peak  is  the  molecular  mass  and  is  at  the  first  peak       *two  peaks  are  important:  one  corresponding  to  molecular  mass  and         the  base  peak  (most  abundant)         *to  find  the  radical,  subtract  base  peak  from  molecular  weight  to  get         the  mass  of  the  radical;  find  the  formula  through  trial  until  the  mass  of       the  formula  is  equal  to  the  masses  that  you  calculated       *break  the  original  bond  with  the  highest  priority  so  you  can  have  the         highest  priority  cation       *first,  focus  on  the  cation  stability  and  if  they’re  the  same,  look  at  the         stability  of  the  radical  when  figuring  out  why  base  peaks  form     -­‐Hydrocarbons       *saturated  has  general  formula  C H n 2n+2       *if  you  have  carbon,  hydrogen,  and  oxygen,  you  always  have  an  even         molecular  mass     -­‐Nitrogen       *molecular  peak  with  an  odd  number  means  we  have  nitrogen       *molecular  peak  with  an  even  number  means  no  nitrogen     -­‐one  CH =one  oxygen   4   -­‐degrees  of  unsaturation     5)  Definitions  to  keep  in  mind     -­‐Molecular  Ion  Peak=molecular  mass  of  compound     -­‐base  peak=most  stable  fragment  that  can  form     6)  Alkyl  Halides:  Identifying  Compounds     -­‐Chlorides       *2  naturally  occurring  isotopes:  35  (most  abundant)  and  37         *get  two  molecular  mass  values       *3:1  ratio  of   Cl: Cl  in  terms  of  abundance       *M=molecular  ion  peak       *M+2  peak  is  the  second  peak  that  is  1/3  the  size  of  M       *if  you  have  two  peaks  at  78  and  80,  then  that  indicates  that  you  have         chlorine  in  your  compound     -­‐Bromides       *2  naturally  occurring  isotopes  that  are  more  even  in  value       *79  and  81       * Br: Br=1:1  ratio       *this  is  how  you  can  tell  if  a  compound  has  bromine  instead  of           chlorine     -­‐When  you  put  CH CHCH Cl  into  the 3  machine,  you 3  lose  electrons       *the  Cl-­‐C  bond  is  broken  because  it’s  the  weakest;  break  away  both         electrons       *get  CH CHCH  w3th  a  mass 3of  43,  which  accounts  for  the  peak  at  43         and  a  Cl  radical       *also  break  a  C-­‐C  bond  which  explains  the  peak  at  63       *this  all  happens  because  of  resonance  structures     -­‐heterolytic  cleavage=breaking  bond  between  two  things  that  are  different       *Pathway  one       *Alpha       *double  hooks     -­‐homolytic  cleavage=breaking  bond  between  two  things  that  are  the  same       *Pathway  two       *Beta       *single  hook     -­‐halides=heterolytic       *halide  is  lost  as  radical  most  often  because  of  bond  strength  and         that’s  what’s  responsible  for  base  peak     7)  Ethers:  Identifying  Compounds     -­‐break  C-­‐O  bond  with  a  double  hooked  arrow       *heterolytic  cleavage       *the  oxygen  becomes  the  radical       *get  another  carbo-­‐cation  as  well     -­‐can  break  on  right  or  left  of  the  oxygen     8)  Alcohols:  Identifying  Compounds     -­‐put  in  the  mass  spectrometer,  an  electron  comes  off  of  the  oxygen,  and  is     replaced  with  a  cation     -­‐alcohol  doesn’t  fall  off  easily  because  they’re  very  electronegative     -­‐homolytic  cleavage  happens  because  alcohol  is  a  poor  leaving  group     -­‐fragment  by  the  beta  carbon  and  one  electron  goes  to  each  side       *get  a  radical  on  both  carbons     9)  Electromagnetic  Spectrum     -­‐mass  spectrometer  doesn’t  help  figuring  out  what  functional  groups  are     present     10)  Wave  Characteristics:  Identifying  Compounds     -­‐wavelength,  frequency     -­‐relationships       *wavelength+frequency=speed  of  light       *E=hv         ^h=Planck’s  Constnat       *E=hc/wavelength     11)  Infrared  Spectroscopy     -­‐smaller     -­‐bonds  aren’t  static     -­‐tells  us  what  functional  groups  we  have  in  our  sample     12)  Functional  Group  Identification     -­‐match  things  to  the  table     -­‐team  this  information  with  the  mass  spectrometer     -­‐alcohol  has  a  big  peak     -­‐amine  has  a  similar  peak  to  alcohol,  just  slightly  smaller   3 2   -­‐find  sp ,  sp ,  and  sp  to  know  if  there’s  a  double  bond     -­‐fingerprint  region=advanced,  so  we  ignore  it     -­‐IR  doesn’t  tell  you  how  many  alcohols  you  have  or  structures       *not  as  much  functionalism        


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