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Number of optically active compounds among the products of ozonolysis


Optical isomerism in Co-ordination CompoundsPredicting reaction among compoundsCan a system of 2 consecutive Biphenyl systems be optically active , even if any adjacent biphenyl systems arent optically active?Can the following compound having a centre of symmetry be called both optically inactive and meso?Is the product of Lindlar hydrogenation of (2Z,4S)-4-methylhept-2-en-5-yne optically active?Why are optically active compounds abundant in nature?Are compounds containing active methylene groups positive for the haloform test?Is trans-1,2-dimethylcyclopropane optically active or not?How to find the number of optically active and optically inactive isomers for a spiropentane derivative?How many stereoisomers can exist for 4,5-bis(3-hydroxyoct-1-en-1-yl)cyclopentane-1,3-diol?






.everyoneloves__top-leaderboard:empty,.everyoneloves__mid-leaderboard:empty,.everyoneloves__bot-mid-leaderboard:empty margin-bottom:0;








2












$begingroup$



The number of optically active compound(s) obtained upon complete ozonolysis of
the following optically active compound is



(1E,3R,4Z,6S,7E,10S,11Z,13S)-3,6,10,13-tetramethylcyclotetradeca-1,4,7,11-tetraene




In the question, I broke all the double bonds and added a $ce-CHO$ group according to the question (ozonolysis).
Checking for the optically active compounds I found two of them:



products



But the solution has given only one compound! Can you please help me with this?










share|improve this question











$endgroup$


















    2












    $begingroup$



    The number of optically active compound(s) obtained upon complete ozonolysis of
    the following optically active compound is



    (1E,3R,4Z,6S,7E,10S,11Z,13S)-3,6,10,13-tetramethylcyclotetradeca-1,4,7,11-tetraene




    In the question, I broke all the double bonds and added a $ce-CHO$ group according to the question (ozonolysis).
    Checking for the optically active compounds I found two of them:



    products



    But the solution has given only one compound! Can you please help me with this?










    share|improve this question











    $endgroup$














      2












      2








      2





      $begingroup$



      The number of optically active compound(s) obtained upon complete ozonolysis of
      the following optically active compound is



      (1E,3R,4Z,6S,7E,10S,11Z,13S)-3,6,10,13-tetramethylcyclotetradeca-1,4,7,11-tetraene




      In the question, I broke all the double bonds and added a $ce-CHO$ group according to the question (ozonolysis).
      Checking for the optically active compounds I found two of them:



      products



      But the solution has given only one compound! Can you please help me with this?










      share|improve this question











      $endgroup$





      The number of optically active compound(s) obtained upon complete ozonolysis of
      the following optically active compound is



      (1E,3R,4Z,6S,7E,10S,11Z,13S)-3,6,10,13-tetramethylcyclotetradeca-1,4,7,11-tetraene




      In the question, I broke all the double bonds and added a $ce-CHO$ group according to the question (ozonolysis).
      Checking for the optically active compounds I found two of them:



      products



      But the solution has given only one compound! Can you please help me with this?







      organic-chemistry stereochemistry ozone






      share|improve this question















      share|improve this question













      share|improve this question




      share|improve this question








      edited 5 hours ago









      andselisk

      21.6k7 gold badges75 silver badges144 bronze badges




      21.6k7 gold badges75 silver badges144 bronze badges










      asked 14 hours ago









      Asad AhmadAsad Ahmad

      163 bronze badges




      163 bronze badges




















          2 Answers
          2






          active

          oldest

          votes


















          4












          $begingroup$

          The given answer is correct. The product scheme you drew is correct as well. However, as I marked in your scheme (see below), products A and B are essentially the same enanthiomer (both have (2S)-configuration). The compounds you have drown in right-hand side are also an identical compound, which is not optically active. Therefore, ozonolysis has given only one optically active compound.



          enter image description here






          share|improve this answer











          $endgroup$




















            3












            $begingroup$

            Ozonolysis of the given compound gives $ceI$ , $ceII$ , $ceIII$ and $ceIV$.




            • $ceI$ and $ceII$ are Homomers and have same configuration "S" and therefore identical (as shown in the figure).


            • $ceIII$ and $ceIV$ are achiral . Therefore , the total number of optically
              active compounds formed after ozonolysis is $ce= 1$.

            enter image description here






            share|improve this answer











            $endgroup$















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              2 Answers
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              active

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              2 Answers
              2






              active

              oldest

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              active

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              active

              oldest

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              $begingroup$

              The given answer is correct. The product scheme you drew is correct as well. However, as I marked in your scheme (see below), products A and B are essentially the same enanthiomer (both have (2S)-configuration). The compounds you have drown in right-hand side are also an identical compound, which is not optically active. Therefore, ozonolysis has given only one optically active compound.



              enter image description here






              share|improve this answer











              $endgroup$

















                4












                $begingroup$

                The given answer is correct. The product scheme you drew is correct as well. However, as I marked in your scheme (see below), products A and B are essentially the same enanthiomer (both have (2S)-configuration). The compounds you have drown in right-hand side are also an identical compound, which is not optically active. Therefore, ozonolysis has given only one optically active compound.



                enter image description here






                share|improve this answer











                $endgroup$















                  4












                  4








                  4





                  $begingroup$

                  The given answer is correct. The product scheme you drew is correct as well. However, as I marked in your scheme (see below), products A and B are essentially the same enanthiomer (both have (2S)-configuration). The compounds you have drown in right-hand side are also an identical compound, which is not optically active. Therefore, ozonolysis has given only one optically active compound.



                  enter image description here






                  share|improve this answer











                  $endgroup$



                  The given answer is correct. The product scheme you drew is correct as well. However, as I marked in your scheme (see below), products A and B are essentially the same enanthiomer (both have (2S)-configuration). The compounds you have drown in right-hand side are also an identical compound, which is not optically active. Therefore, ozonolysis has given only one optically active compound.



                  enter image description here







                  share|improve this answer














                  share|improve this answer



                  share|improve this answer








                  edited 11 hours ago

























                  answered 11 hours ago









                  Mathew MahindaratneMathew Mahindaratne

                  10.3k1 gold badge12 silver badges37 bronze badges




                  10.3k1 gold badge12 silver badges37 bronze badges























                      3












                      $begingroup$

                      Ozonolysis of the given compound gives $ceI$ , $ceII$ , $ceIII$ and $ceIV$.




                      • $ceI$ and $ceII$ are Homomers and have same configuration "S" and therefore identical (as shown in the figure).


                      • $ceIII$ and $ceIV$ are achiral . Therefore , the total number of optically
                        active compounds formed after ozonolysis is $ce= 1$.

                      enter image description here






                      share|improve this answer











                      $endgroup$

















                        3












                        $begingroup$

                        Ozonolysis of the given compound gives $ceI$ , $ceII$ , $ceIII$ and $ceIV$.




                        • $ceI$ and $ceII$ are Homomers and have same configuration "S" and therefore identical (as shown in the figure).


                        • $ceIII$ and $ceIV$ are achiral . Therefore , the total number of optically
                          active compounds formed after ozonolysis is $ce= 1$.

                        enter image description here






                        share|improve this answer











                        $endgroup$















                          3












                          3








                          3





                          $begingroup$

                          Ozonolysis of the given compound gives $ceI$ , $ceII$ , $ceIII$ and $ceIV$.




                          • $ceI$ and $ceII$ are Homomers and have same configuration "S" and therefore identical (as shown in the figure).


                          • $ceIII$ and $ceIV$ are achiral . Therefore , the total number of optically
                            active compounds formed after ozonolysis is $ce= 1$.

                          enter image description here






                          share|improve this answer











                          $endgroup$



                          Ozonolysis of the given compound gives $ceI$ , $ceII$ , $ceIII$ and $ceIV$.




                          • $ceI$ and $ceII$ are Homomers and have same configuration "S" and therefore identical (as shown in the figure).


                          • $ceIII$ and $ceIV$ are achiral . Therefore , the total number of optically
                            active compounds formed after ozonolysis is $ce= 1$.

                          enter image description here







                          share|improve this answer














                          share|improve this answer



                          share|improve this answer








                          edited 3 hours ago

























                          answered 3 hours ago









                          Chakravarthy KalyanChakravarthy Kalyan

                          2,6745 silver badges23 bronze badges




                          2,6745 silver badges23 bronze badges



























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