DAT Destroyer (2011) O. Chem. #33

[ucsdstudent01]

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(CH3)2CHCH2CH3 --- Cl2, hv ---> how many stereoisomers?

anybody know why it says that C1 is chiral when Cl is chlorinated on it??? because it would have 2 hydrogens and 1 Cl attached to the Carbon. i get why C3 is chiral. anybody got any answer to this?

 

[Demps]

(CH3)2CHCH2CH3 --- Cl2, hv ---> how many stereoisomers?

anybody know why it says that C1 is chiral when Cl is chlorinated on it??? because it would have 2 hydrogens and 1 Cl attached to the Carbon. i get why C3 is chiral. anybody got any answer to this?

That answer key has to be wrong. I ignored that question when I studied for OC. C1 is clearly achiral.

 

[Jsaxon]

a new chiral center is formed at carbon number 2, as it is attached to 4 different groups, a methyl, methyl-chloride, a hydrogen and an ethyl group. I found this to be tricky too but once you see it, its a real duhhh moment..

 

[ucsdstudent01]

a new chiral center is formed at carbon number 2, as it is attached to 4 different groups, a methyl, methyl-chloride, a hydrogen and an ethyl group. I found this to be tricky too but once you see it, its a real duhhh moment..

wait isnt C2 not chiral because you have 2 groups that are similar... so C2 isnt chiral... because C would be attached to a H and 2 CH3s

 

[jefff]

when you monochlorinate C1, C2 becomes chiral because its not 2 CH3's, its 1 -CH3, 1 -H, 1 -CH2Cl, 1 -CH2CH3

wait isnt C2 not chiral because you have 2 groups that are similar... so C2 isnt chiral... because C would be attached to a H and 2 CH3s

 

[Jsaxon]

Its the wording of the answer that got me, Its not saying Carbon 1 is chiral its saying that out of the 4 possible structures, structure one is chiral. This is what confused me

 

[Demps]

Its the wording of the answer that got me, Its not saying Carbon 1 is chiral its saying that out of the 4 possible structures, structure one is chiral. This is what confused me

hahahah I see it now too lol!

 

[ucsdstudent01]

ooooooo okay. shoot sorry sorry im stupid. Thanks alot guys ^^

 

[NewBee12]

When you hit C-1 we generate chirality at C-2. The rest of the stereoisomers are in the solution.
Very tricky problem indeed. It got me too the first time I looked at it.