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Organic Chemistry

Hot goIITian

Joined: 20 Jun 2008
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29 Jun 2008 15:23:10 IST
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total number of isomers
None

Is there any specific formula to find the total number of isomers(structural+stereo)?


It is time consuming for me to sketch down all isomers if I'm given a 15 or 20 carbon molecule


 


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arushi varshney's Avatar

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Joined: 11 May 2008
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29 Jun 2008 17:28:26 IST
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there is no specific formula for structural isomers.,...the've to be drawn and seen....


though you can always check the D.B.E. (double bond equivalent     = C + 1 -  ( H + X - N)/ 2


C= NO OF CARBONS


H = HYDROGENS


X= HALOGENS


N= NITROGEN


THIS NO. IS THE AMOUNT OF 'UNSATURATION' e.g.  if DBE= 2 either there are 2 pi bonds (i.e. 2 double bonds or one triple bond ) or one ring and one pi or 2 rings.......THIS MAKES IT SOMEWHAT EASY AS U KNOW WHICH TYPE  OF COMPD. U CAN TRY  THINKING OF....(though in most  problems compd. given is an alkane so u'll have to draw and see)


IF ONLY STEREOISOMERS ARE CONCERNED...


no. of G.I. = 2N IF END GROUPS OF THE DOUBLE BOND ARE DIFFERENT


no of G.I. = 2(N-1)  +  2(P-1) IF THEY ARE IDENTICAL


N = CONTRIBUTING DOUBLE BONDS


P= N/2 IF N IS EVEN


     OR (N+1)/2  IF  N  IS  ODD


SAME IS APPLICABLE FOR OPTICAL ISOMERS WHERE U KEEP N = NO. OF CHIRAL CARBONS.....


O.I. = 2N IF SYMMETRY IS NOT PRESENT IN ANY FORM OF THE MOLECULE


O.I. = 2(N-1) + 2(P-1) IF SYMMETRY IS PRESENT IN SOME FORM OF THE MOLECULE


p.s :   total stereo isomers = no. of  G.I. * no. of O.I.   (coz i used to make the mistake of adding them!!)


 

Tarin Bansal's Avatar

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Joined: 27 Jul 2007
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29 Jun 2008 18:55:03 IST
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I dont know whether there is any such formula but the best and safest way is to draw and then calculate.


And for ur question, I dont think any gud level exam will give u a molecule with 15-20 C atoms. Only bullsh*t exams can do this thing. Gud exams(like JEE, AIEEE, BITSAT) want to u to draw and then calculate and hence make mistakes(remember that competitive exams, dont select the students, they reject them).


So practice a lot of such questions by drawing all the possible isomers.


Start from the C at one end and with the longest possible chain. And keep shortening the chain as u draw more compounds. Go step by step, u will never miss any isomer and will always get ur answer right.


Hope it helps.

arushi varshney's Avatar

New kid on the Block

Joined: 11 May 2008
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29 Jun 2008 20:10:28 IST
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yeah 15-20 c prob. is unlikely to be asked....but do consider the prob.


Me-CH=C=C=CH-CH(Cl)-CH=CH-Cl   TO calculate stereo isomers...


G.I. = 4


O.I.=2


S.I. = 8    U CAN FIND OUT IN NO TIME.(which is what matters)....and in probs where simple alkane is given draw and see....this just helps in stereo isomers....


Hot goIITian

Joined: 20 Jun 2008
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29 Jun 2008 20:25:07 IST
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Does the compound you have mentioned existing?


 

Tarin Bansal's Avatar

Blazing goIITian

Joined: 27 Jul 2007
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29 Jun 2008 20:32:35 IST
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Yes, the compound can exist.
Why? U have any doubt abt its existence??

Scorching goIITian

Joined: 23 May 2008
Posts: 220
2 Jul 2008 17:12:33 IST
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the totoal no of optical isomers is 2^n+1 where n is no of chiral carbons




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