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picture1_Aldol Condensation Ppt 82056 | Week12 Synthesis Dibenzalacetone F18


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File: Aldol Condensation Ppt 82056 | Week12 Synthesis Dibenzalacetone F18
schedule of day ppe check at the door pre lab check at the door quiz recitation synthesis of dibenzalacetone safety put bags away goggles gloves lab coat lab due dates ...

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              Schedule of day:
      ■ PPE check – at the door
      ■ Pre-lab check – at the door
      ■ Quiz
      ■ Recitation
        – Synthesis of Dibenzalacetone
      ■ Safety
        – Put bags away
        – Goggles
        – Gloves
        – Lab Coat
      ■ LAB!
                                           Due Dates
              ■Today
                   – Synthesis of Banana Oil Report due
                   – End of lab – notebook copy pages (Synthesis of 
                       dibenzalacetone)
              ■Next Week
                   – At the beginning of lab – Synthesis of Dibenzalacetone Report
                       •   See “Notebook & Report Formats” on Bb for instructions for a 
                           synthesis report.
              ■Two Weeks
                   – Final Exam
             Synthesis of Dibenzalacetone
           ■
              This reaction is an example of an aldol 
              condensation.
                   O
                   C          O                             O
                      H               NaOH
           2            + CH C CH                    CH=CH C CH=CH
                            3     3
           ■
              The reaction is also a mixed aldol, between and 
              aldehyde and a ketone.
           ■
              The product is quite stable because of 
              conjugation (resonance stabilization), and so 
              product formation is highly favored. 
                 Synthesis of Dibenzalacetone
          ■Only the ketone has an alpha-H that can be 
                                             -
               removed by OH base to form the enolate:
                                 O                                          O                     O
                          
          HO         H CH C CH                           HO           CH C CH              CH C CH
                             2          3                  2             2          3          2         3
          ■ O                             O                                      O         O
               The carbonyl group in the aldehyde is more 
              Ph C H               CH C CH                                  Ph C CH C CH
                                       2          3                                      2          3
               reactive than the carbonyl of the ketone:
                                                                                 H
                  Synthesis of Dibenzalacetone
           ■The tetrahedral intermediate from addition is 
                protonated:
                                                                        H
                    O         O                                            O         O
                                                                               
                                The tetrahedral intermediate from 
               Ph C CH C CH HO                                        Ph C CH C CH                  HO
                            2          3     2                                      2         3
                                addition is protonated:
                    H                                                      H
                 H
                    O                                                            O
                              O                                             
           ■                                                            
                          
                Then dehydration occurs to give a stable conjugated 
                                                                  Ph C CH C CH HO                   HO
               Ph C CH C CH                 HO                                          3    2
                                      3
                                                                       H
                product (a,b-unsaturated ketone):
                    H H
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...Schedule of day ppe check at the door pre lab quiz recitation synthesis dibenzalacetone safety put bags away goggles gloves coat due dates today banana oil report end notebook copy pages next week beginning see formats on bb for instructions a two weeks final exam this reaction is an example aldol condensation o c h naoh ch also mixed between and aldehyde ketone product quite stable because conjugation resonance stabilization so formation highly favored only has alpha that can be removed by oh base to form enolate ho carbonyl group in more ph reactive than tetrahedral intermediate from addition protonated then dehydration occurs give conjugated b unsaturated...

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