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    Chapter1 Bonding and Isomerism Practice2

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    This document provides a worksheet on organic chemistry concepts including: 1) Naming organic compounds and identifying constitutional isomers 2) Distinguishing between constitutional, conformational, and configurational isomers 3) Explaining polar reactions in terms of partial charges and curly arrows to show electron movement between nucleophiles and electrophiles. Students are directed to practice these skills further.

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    Chapter1 Bonding and Isomerism Practice2

    Uploaded by

    sug
    11 views4 pages
    This document provides a worksheet on organic chemistry concepts including: 1) Naming organic compounds and identifying constitutional isomers 2) Distinguishing between constitutional, conformational, and configurational isomers 3) Explaining polar reactions in terms of partial charges and curly arrows to show electron movement between nucleophiles and electrophiles. Students are directed to practice these skills further.

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    This document provides a worksheet on organic chemistry concepts including: 1) Naming organic compounds and identifying constitutional isomers 2) Distinguishing between constitutional, conformational, and configurational isomers 3) Explaining polar reactions in terms of partial charges and curly arrows to show electron movement between nucleophiles and electrophiles. Students are directed to practice these skills further.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    11 views4 pages

    Chapter1 Bonding and Isomerism Practice2

    Uploaded by

    sug
    This document provides a worksheet on organic chemistry concepts including: 1) Naming organic compounds and identifying constitutional isomers 2) Distinguishing between constitutional, conformational, and configurational isomers 3) Explaining polar reactions in terms of partial charges and curly arrows to show electron movement between nucleophiles and electrophiles. Students are directed to practice these skills further.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
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    CHEM1002 Worksheet 2: Bonding and Isomerism

    Model 1: Naming Organic Compounds


    Critical thinking questions
     
    1. You   find   a   bottle   in   the   lab   labeled   dimethylpentane.   This   name   is   ambiguous,   so   draw   (using  
    stick  notation)  all  the  possible  structures  consistent  with  this  name.  
     
     
     
     
     
     
     
     
     
     
     
     
     
     
     
    2. You  should  have  drawn  4  structures  in  Q3.  Pick  one  of  these  and  try  to  give  it  an  unambiguous  
    name.  
     
     
     
     
    Convention  has  it  that  compounds  are  numbered  from  the  end  nearest  the  functional  group  that  
    provides  the  root  of  the  name  (the  alkene  in  1-­‐butene,  the  alcohol  of  1-­‐butanol).  Where  there  are  no  
    such  functional  groups,  numbering  of  the  parent  chain  starts  from  the  end  nearest  a  branch.  
     
    3. Is  your  answer  to  Question  2  consistent  with  this  convention?  If  not,  try  to  name  it  again.  
     
     
     
     
    4. Name  the  other  molecules  in  your  answer  to  Question  1.  
     
     
     
     
     
     
     
     
     
     
     
     
    Learning  to  name  organic  molecules  is  a  bit  like  learning  a  foreign  language.  There  is  no  substitute  for  
    practice!  
    Model 2: Isomerism
    There are three broad classes of isomers.

    Constitutional Conformational Configurational


    • Constitutional isomers have the same formula but different connectivity.
    • Conformational isomers differ only by rotation about a single bond. They interconvert freely at all
    but extremely low temperatures (ie they are identical).
    • Configurational isomers (stereoisomers) have the same connectivity but cannot be interconverted
    through single bond rotation. Bond breaking and bond formation are required for interconversion.
    Here are some molecules all with the formula C5H9ClO

     
    Critical thinking questions
     
    1. With  the  help  from  the  others  in  your  group,  identify  and  circle  at  least  7  constitutional  isomers  
     
    2. Identify  and  draw  two  pairs  of  conformational  isomers  
     
     
     
     
     
     
    3. Identify  and  draw  three  pairs  of  configurational  isomers.    
     
     
     
     
     
     
    4. Extension:  How  many  different  functional  groups  can  you  identify?  
     
     
     
    Model 3: Polar Reactions
    In   many   covalent   bonds,   the   electrons   are   not   distributed   evenly   due   to   differences   in   the  
    electronegativity   of   the   two   atoms   involved.   We   use   partial   charges   (δ+,   δ-­‐)   to   denote   the   resultant  
    polarisation   of   the   bond.   C   and   H   have   very   similar   electronegativities   and   so   C-­‐H   bonds   are  
    approximately  non-­‐polar.    
     
     
    Critical thinking questions

    1. Determine  the  partial  charges  on  the  atoms  in  the  following  molecules.    

     
     
    2. We   know   that   there   is   an   attractive   force   between   positively   and   negatively   charged   objects.  
    With   this   in   mind,   it   would   seem   sensible   that   the   negatively   charged   nitrogen   below   would  
    react  with  the  slightly  positive  carbon  of  the  carbonyl.  
     

     
     
    We   know   from   Worksheet   1   that   carbon   typically   forms   four   bonds.   If   we   form   a   new   bond  
    between  the  nitrogen  and  the  carbonyl  carbon  what  else  needs  to  happen?  
     
     
     
    3. Which  bond  most  is  likely  to  break  and  why?  
     
     
     
     
     
    Chemists  use  “curly  arrows”  to  track  the  movement  of  electrons  in  a  reaction.  Convention  has  it  that  
    the  arrow  starts  at  the  source  of  the  electrons  (a  lone  pair  or  a  bond)  and  finishes  where  the  electrons  
    end  up  (in  a  bond  or  as  a  lone  pair  on  an  atom).  
     

     
     
    4. Try  using  curly  arrows  to  describe  the  movement  of  electrons  in  the  reaction  below.    
     

     
     
    This  is  an  example  of  a  polar  reaction,  the  most  common  type  of  reaction  in  organic  chemistry  (and  
    the   only   kind   you   will   see   this   year).   Polar   reactions   always   involve   the   interaction   between   an  
    electron  rich  component  (nucleophile)  and  an  electron  deficient  component  (electrophile).  
     
     
     
    5. Identify  the  electrophile  and  the  nucleophile  in  two  reactions  above.  
     
    6. Draw in appropriate partial charges (δ and δ ) and curly arrows to show the mechanism of the
    following reactions. Classify the starting materials as nucleophile, electrophile or neither, indicating
    your choice underneath each reactant.

    CH3 H CH3
    Br
    CH3 N + H C Br CH3 N CH3
    CH3 H CH3  
     
     
    H  3C  
      H  3C  
      H  3C  
     
    +   C   O   H   C   O   H  
    H   H   C   O  
    H  3C  
      H  3C  
      H  3C  
      H  

     
     
     
     
     
     
     
     
     
     
     
    What  is  the  recipe  for  success?  
    Practice  further  by  completing  this  week’s  tutorial  homework  and  suggested  exam  questions.  

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