Are all alkene geometrical isomers achiral?

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I was reading a book and it tells that alkene geometrical isomers are achiral.
I wanted to know that is it applicable for alkene geometrical isomers?
Thanks in advance.










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  • 4




    $begingroup$
    You want a rule which is not there. Alkenes, like nearly all other classes of organic compounds, may or may not be chiral. Let's put it this way: having a double bond is irrelevant to chirality.
    $endgroup$
    – Ivan Neretin
    Jan 14 at 13:06










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    The statement in your book is a truism: Correct, but does not transport any additional insight into the underlying concepts. Except as an exercise question: Why do these isomers not show a stereoisomery?
    $endgroup$
    – Karl
    Jan 14 at 21:51










  • $begingroup$
    @Karl Sadly, that statement isn't true. See my answer below...
    $endgroup$
    – Zhe
    Jan 16 at 14:27










  • $begingroup$
    @Zhe I would say that calling a cumulated diene an alkene is also a truism: Correct, but not at all helpful. ;-) If it is correct. Because the central carbon atom is sp hybridised.
    $endgroup$
    – Karl
    Jan 16 at 22:15











  • $begingroup$
    Such questions always remind me of this one, no offence intended: xkcd.com/169
    $endgroup$
    – Karl
    Jan 16 at 22:19















1












$begingroup$


I was reading a book and it tells that alkene geometrical isomers are achiral.
I wanted to know that is it applicable for alkene geometrical isomers?
Thanks in advance.










share|improve this question









$endgroup$







  • 4




    $begingroup$
    You want a rule which is not there. Alkenes, like nearly all other classes of organic compounds, may or may not be chiral. Let's put it this way: having a double bond is irrelevant to chirality.
    $endgroup$
    – Ivan Neretin
    Jan 14 at 13:06










  • $begingroup$
    The statement in your book is a truism: Correct, but does not transport any additional insight into the underlying concepts. Except as an exercise question: Why do these isomers not show a stereoisomery?
    $endgroup$
    – Karl
    Jan 14 at 21:51










  • $begingroup$
    @Karl Sadly, that statement isn't true. See my answer below...
    $endgroup$
    – Zhe
    Jan 16 at 14:27










  • $begingroup$
    @Zhe I would say that calling a cumulated diene an alkene is also a truism: Correct, but not at all helpful. ;-) If it is correct. Because the central carbon atom is sp hybridised.
    $endgroup$
    – Karl
    Jan 16 at 22:15











  • $begingroup$
    Such questions always remind me of this one, no offence intended: xkcd.com/169
    $endgroup$
    – Karl
    Jan 16 at 22:19













1












1








1





$begingroup$


I was reading a book and it tells that alkene geometrical isomers are achiral.
I wanted to know that is it applicable for alkene geometrical isomers?
Thanks in advance.










share|improve this question









$endgroup$




I was reading a book and it tells that alkene geometrical isomers are achiral.
I wanted to know that is it applicable for alkene geometrical isomers?
Thanks in advance.







stereochemistry






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share|improve this question











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asked Jan 14 at 12:49









Abhay SharmaAbhay Sharma

91




91







  • 4




    $begingroup$
    You want a rule which is not there. Alkenes, like nearly all other classes of organic compounds, may or may not be chiral. Let's put it this way: having a double bond is irrelevant to chirality.
    $endgroup$
    – Ivan Neretin
    Jan 14 at 13:06










  • $begingroup$
    The statement in your book is a truism: Correct, but does not transport any additional insight into the underlying concepts. Except as an exercise question: Why do these isomers not show a stereoisomery?
    $endgroup$
    – Karl
    Jan 14 at 21:51










  • $begingroup$
    @Karl Sadly, that statement isn't true. See my answer below...
    $endgroup$
    – Zhe
    Jan 16 at 14:27










  • $begingroup$
    @Zhe I would say that calling a cumulated diene an alkene is also a truism: Correct, but not at all helpful. ;-) If it is correct. Because the central carbon atom is sp hybridised.
    $endgroup$
    – Karl
    Jan 16 at 22:15











  • $begingroup$
    Such questions always remind me of this one, no offence intended: xkcd.com/169
    $endgroup$
    – Karl
    Jan 16 at 22:19












  • 4




    $begingroup$
    You want a rule which is not there. Alkenes, like nearly all other classes of organic compounds, may or may not be chiral. Let's put it this way: having a double bond is irrelevant to chirality.
    $endgroup$
    – Ivan Neretin
    Jan 14 at 13:06










  • $begingroup$
    The statement in your book is a truism: Correct, but does not transport any additional insight into the underlying concepts. Except as an exercise question: Why do these isomers not show a stereoisomery?
    $endgroup$
    – Karl
    Jan 14 at 21:51










  • $begingroup$
    @Karl Sadly, that statement isn't true. See my answer below...
    $endgroup$
    – Zhe
    Jan 16 at 14:27










  • $begingroup$
    @Zhe I would say that calling a cumulated diene an alkene is also a truism: Correct, but not at all helpful. ;-) If it is correct. Because the central carbon atom is sp hybridised.
    $endgroup$
    – Karl
    Jan 16 at 22:15











  • $begingroup$
    Such questions always remind me of this one, no offence intended: xkcd.com/169
    $endgroup$
    – Karl
    Jan 16 at 22:19







4




4




$begingroup$
You want a rule which is not there. Alkenes, like nearly all other classes of organic compounds, may or may not be chiral. Let's put it this way: having a double bond is irrelevant to chirality.
$endgroup$
– Ivan Neretin
Jan 14 at 13:06




$begingroup$
You want a rule which is not there. Alkenes, like nearly all other classes of organic compounds, may or may not be chiral. Let's put it this way: having a double bond is irrelevant to chirality.
$endgroup$
– Ivan Neretin
Jan 14 at 13:06












$begingroup$
The statement in your book is a truism: Correct, but does not transport any additional insight into the underlying concepts. Except as an exercise question: Why do these isomers not show a stereoisomery?
$endgroup$
– Karl
Jan 14 at 21:51




$begingroup$
The statement in your book is a truism: Correct, but does not transport any additional insight into the underlying concepts. Except as an exercise question: Why do these isomers not show a stereoisomery?
$endgroup$
– Karl
Jan 14 at 21:51












$begingroup$
@Karl Sadly, that statement isn't true. See my answer below...
$endgroup$
– Zhe
Jan 16 at 14:27




$begingroup$
@Karl Sadly, that statement isn't true. See my answer below...
$endgroup$
– Zhe
Jan 16 at 14:27












$begingroup$
@Zhe I would say that calling a cumulated diene an alkene is also a truism: Correct, but not at all helpful. ;-) If it is correct. Because the central carbon atom is sp hybridised.
$endgroup$
– Karl
Jan 16 at 22:15





$begingroup$
@Zhe I would say that calling a cumulated diene an alkene is also a truism: Correct, but not at all helpful. ;-) If it is correct. Because the central carbon atom is sp hybridised.
$endgroup$
– Karl
Jan 16 at 22:15













$begingroup$
Such questions always remind me of this one, no offence intended: xkcd.com/169
$endgroup$
– Karl
Jan 16 at 22:19




$begingroup$
Such questions always remind me of this one, no offence intended: xkcd.com/169
$endgroup$
– Karl
Jan 16 at 22:19










1 Answer
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While in general, you should consider chirality and alkene geometry as orthogonal concepts, the statement in your question isn't even true.



Consider the case of 2,3-pentadiene, aka, 1,3-dimethylallene. This compound is chiral. Any change in the geometry of either of the double bonds provides the other enantiomer.



2,3-pentadiene






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    1 Answer
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    active

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    active

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    6












    $begingroup$

    While in general, you should consider chirality and alkene geometry as orthogonal concepts, the statement in your question isn't even true.



    Consider the case of 2,3-pentadiene, aka, 1,3-dimethylallene. This compound is chiral. Any change in the geometry of either of the double bonds provides the other enantiomer.



    2,3-pentadiene






    share|improve this answer









    $endgroup$

















      6












      $begingroup$

      While in general, you should consider chirality and alkene geometry as orthogonal concepts, the statement in your question isn't even true.



      Consider the case of 2,3-pentadiene, aka, 1,3-dimethylallene. This compound is chiral. Any change in the geometry of either of the double bonds provides the other enantiomer.



      2,3-pentadiene






      share|improve this answer









      $endgroup$















        6












        6








        6





        $begingroup$

        While in general, you should consider chirality and alkene geometry as orthogonal concepts, the statement in your question isn't even true.



        Consider the case of 2,3-pentadiene, aka, 1,3-dimethylallene. This compound is chiral. Any change in the geometry of either of the double bonds provides the other enantiomer.



        2,3-pentadiene






        share|improve this answer









        $endgroup$



        While in general, you should consider chirality and alkene geometry as orthogonal concepts, the statement in your question isn't even true.



        Consider the case of 2,3-pentadiene, aka, 1,3-dimethylallene. This compound is chiral. Any change in the geometry of either of the double bonds provides the other enantiomer.



        2,3-pentadiene







        share|improve this answer












        share|improve this answer



        share|improve this answer










        answered Jan 14 at 14:19









        ZheZhe

        12.2k12450




        12.2k12450



























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