Page 1082 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg
P. 1082

1066                    c.

     CHAPTER 11                         CH 3
                                                Bu SnH
     Free Radical Reactions                       3
                              NC        C  NO 2           NC        CH(CH )
                                                                         3 2
                                                (PhCO )
                                                     2 2
                                        CH 3
                             d.

                                                                    °
                                                                 – 78 C
                               CH 3 (CH 2 ) 5 CH     CH 2 +  ClNHCO 2 C 2 H 5 +  Cr(II)  CH 3 (CH 2 ) 5 CHCH 2 NHCO 2 C 2 H 5
                                                                              Cl



                             e.

                                      CH 3                                 H C  CH 3
                                                                            3
                                                         –
                               N      C  NO 2  +  N     C (CH )       N      C  C      N
                                                             3 2
                                      CH 3                                 H 3 C  CH 3


                             f.

                                 OH                    O            O
                                          electrolysis
                               PhCCH(CH )            PhCCH    +   CH 3 CNHCH(CH )
                                       3 2
                                           CH CN          3                  3 2
                                             3
                                CH 3

                             g.


                                                  CH 3  CH
                                  CH 3                    3
                              CH 3    CH   100°C
                                        2
                                                  Ph
                                Ph


                             h.

                                                  PhSH
                             H C      CHCH CH    C(CH )  PhSCH 2    C(CH )
                                                                        3 2
                                      2
                              2
                                               3 2
                                                   O 2
                                                               O  O
                                                                    OH
                        11.7. The decarbonylation of the two isotopically labeled pentenals shown below
                             have been studied. Explain why the distribution of deuterium found in the
                             products is affected by solution concentration.
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