the right hand side and left hand side of

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					1. a) For each section below, choose the arrows that best describe the relationship between
the right hand side and left hand side of the equation by putting a letter in the central boxes.

 Choices:
                       A                        B          C               D                    E
                                                                                          (no reaction/
                                                                                          interconversion)
i)

                 OH +               N           Na+                       O Na+       +         NH



ii)                                                                       +


                                        +

iii)                         CH3                                          CH3
                                            H                                         H
                      H                         CH3                H                      H
                       H3C                                          H3C
                                    H                                           CH3
iv)
            NH                      O                                     NH                      O
                       +                                                              +
                 NH                         NH2                                 NH2                   NH



b) Name the functional groups circled in the molecule shown below.



                                                      HN
                                H

                                                               O
                        O


                                                               C   N



                                        O                  O

                            O



                                                                                                        2.....
c) Redraw compound 1, clearly showing it in its most stable conformation. If more than
one structure is drawn please circle your final answer.


                 OH
  HO                  OH



  HO                  OH

                 OH
        compound 1



d). Draw the meso form of 2,3-dibromobutane using the template below. Indicate the
absolute configuration at each stereogenic center as being either (R) or (S).



                                H3C


                                             CH3




2. a) Name the following compounds using IUPAC nomenclature, including as necessary
   designation of stereochemistry.

 i)


        Br

 ii)
             H




 iii)

                           OH



                                                                                     3.....
b) Draw all of the stereoisomers of 1,2,3-trichlorocyclopentane (note substitution pattern!).
Start with the template below and redraw as necessary. Draw each isomer only once and
show stereochemistry where appropriate using "wedges" and "dashes".




c). Draw two resonance structures that contribute most to the overall picture of nitromethane
(CH3NO2). In each structure, clearly show all lone pairs and formal charges.




                                                                                        4.....
3. a) Draw a transition state for the following reaction in the box below. Clearly show the
expected geometry.

              H                                          H
                                                                   +
                      Br      +     NH3                          NH3 +     Br
          H                                          H
              H                                           H




                                      transition state

b) Treatment of Compound 1 with methanethiolate (CH3S-) gave a single isomer of
compound 2. Draw a mechanism for the reaction (no transition state(s) required),
and clearly show the structure and stereochemistry of compound 2.

              O                             +
                      O              CH3S Na
                                                         Compound 2
                                                         (single isomer)
         H                    CH3
         H3C              H
                  1




                                                                                       5.....
c) Draw a detailed mechanism for the reaction shown below. It is not necessary to
show any transition states.

                       CH3                                  CH3
                                     H   +     HO             O
    HO                     O

             3                                      4




 d) Which compound is present in a greater amount at equilibrium, 3 or 4?

                  answer =

  Briefly explain your reasoning.




                                                                                    The End