dat 2010 Destroyer organic question number 23

[vash429]

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23. Consider the monochlorination of 2 - methylbutane. How many products are expected if stereoisomers were counted?
Answer: 6

I don’t see how image (I) has an enantiomer (when Cl is attached to carbon number 1.) That carbon center has a C, Cl and H; not 4 groups so it should not be chiral.

 

[blackberryman]

THe answer is 4 not 6.

 

[Blue87Fiero]

It is 6 you create a chiral carbon at carbon 1 and 3.

 

[blackberryman]

Sorry I didnt see the "were counted" part

 

[Blue87Fiero]

I think six again

 

[Adamsswag]

Six products here. Keyword here are "stereoisomers" and enantiomers are stereoisomers. So when counting the number of stereoisomers produced by a reaction, if a product has a chirality center, include its enantiomer. Therefore, we have 4 structurally different stereoisomers and of the 4, 2 (I and III as viewed in the solutions) have chirality centers (accounts for an enantiomer of each structure), and so 4 + 2 = 6

 

[vash429]

Thanks everyone I was not seeing one of the enantiomers got it now.