Page 15 - Medicinal Chemistry Self Assessment
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4      Medicinal Chemistry Self Assessment
          Structures for 1.1 and 2.1

          The bold has been removed.  The exact same structures are in both of these chapters, but I have provided two
                b.  For each of the functional groups you identified, indicate if it is hydrophilic or hydrophobic in
                   character. Also provide a brief explanation for your response.
          copies in the event you wanted that.
             Box           Hydrophilic or Hydrophobic
                   A
                   B
                        A
                  C                                                                             F
                  D                          C
                   E
                                                                             E
                   F
                  G                                              D
               Warfarin                                                              Bromfenac          G
                  H             B
                                                    Phenytoin
                   I
                   J

                   K
                        H
                   L
                                                 J          K
                            I                                         L
                                                      Salmeterol

            2.  Shown below are the structures of ibuprofen and sulfamethoxazole. Four functional groups have
                been highlighted. Based on their electronic properties AND their relative positions in the molecule,

                identify if they are electron withdrawing or electron donating. Additionally, identify if this effect is
                due to resonance or induction.

                                             B                                          D
                          A                                                  O
                                             O                 C                            CH  3
                                                             H 2 N           S   N
                                          OH                                     H    N  O
                                                                             O

                                 Ibuprofen                            Sulfamethoxazole




















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