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Organic Chemistry

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Hot goIITian

Joined: 26 May 2008
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25 Dec 2008 07:43:17 IST
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========OPTICAL ISOMERISM : 3 VRY VRY URGENT DOUBTS=========
None

D1: In the following organic compound [ in  fig -1] ....the QUESTION IS TO IDENTIFY WHETHER THE PAIR IS AN ENANTIOMER OR THEY ARE IDENTICAL...or not. ANSWER  GIVEN IS ENANTIOMERS...BUT WHY CAN'T WE ROTATE THE COMPOUND IN THE RIGHT [WHOLE COMPOUND] WITHOUT DISPLACING NEITHER THE BONDS NOR THE ATOMS ,ie , 180 degrees...then we will get the same compound in the right...???


 


FIG -1:


 



 


D2: The question is to mark the asymmetric atoms and give the no: of OPTICAL ISOMERS in the compound HOOC-(COOH)2-COOH...So IF WE DRAW THE DIAGRAM LIKE THE ONE  IN THE RIGHT [ OF FIG-2] WE WILL GET A PLANE OF SYMMETRY...BUT IF WE DRAW IT LIKE IN THE LEFT THEN WE WON'T GET A PLANE OF SYMMETRY ...why...or is it my wrong understanding ???


 


 FIG-2:


 


IG-2:


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Comments (7)


Cool goIITian

Joined: 12 Aug 2007
Posts: 41
25 Dec 2008 23:41:41 IST
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1)Because ficsure projection formula prevents you from rotating the compounds out of the plane of paper.If you make models of the compound u will realise tht the atoms are in different planes and 180 degree rotations change the relative position of the atoms with respect to each other.


tell me if i am right or wrong.


rate if usefull


Cool goIITian

Joined: 12 Aug 2007
Posts: 41
25 Dec 2008 23:52:33 IST
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2) in any compound there are two 2^n optical isomers.here n is 2.therefore there should hav been 4 optical isomers.


But for the given compound 2 forms( (2) and it's mirror image) are optical isomers.The other two ((2) and its mirror image) are mesomers and are optically inactive.It only has 2 optical isomers.


again tell me if i am right and rate me if useful

sajal kumar's Avatar

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26 Dec 2008 12:38:36 IST
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you cant rotate the compound out of the plane of the paper rotating in the plane doesnt give u the same compound

JSG's Avatar

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26 Dec 2008 19:37:18 IST
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no no imean rotating right along the paper just like you rotate a screw into a cardboard...am i wrong ??
JSG's Avatar

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27 Dec 2008 15:58:37 IST
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MORE ANS.. PLEASE....ALL ANSWERS WILL BE GIVEN 5 POINTS...please explain with details after downloading the pic..plzz!!!

Cool goIITian

Joined: 12 Aug 2007
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27 Dec 2008 16:53:55 IST
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they r both the same.rotating out of the plane of paper and rotating like wat u said finally gives a different compound(enantiomer of the given compound)


if u imagine three dimensionally, groups on the horizontal lines point towards u out of the plane of paper and vertical u'll know tht the compound will be diff from the given compound in spatial orientation after 180 degree rotation


experts, please correct if i am wrong


Cool goIITian

Joined: 27 Dec 2008
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27 Dec 2008 17:24:26 IST
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well according to me they are the same two molecules....as on 180 degree rotation in the plane of the papaer, same structure is obtained...this can be best examplified...as in case of organic compounds having enantiomeic pairs....,rotation doesn't play any role...rotating a molecule and obtaining a symmetrical structure clearly shos that the compound has an element of symmetry which makes it achiral....or optically inactive......

other way to understand this is through (RS) system of nomenclature....if the (RS) nomenclature for both the compounds is same,then,it clearly shows that the two structures are similar....which is true in this case......by the way,is this question taken from any book????????????????????????????



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