OChem Question 4 from destroyer

[omgdats]

Hi,
I tried to search for this question, but i couldn't find it, so this problem must be really easy. But how does monochlorination of 2 methybutane result in 6 stereoisomers? thanks

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[alanan84]

Double check the question, it would result in 4 stereoisomers.

 

[Shinpe]

6 is correct. chlorination at C-1 makes C-2 a chiral center, so that will give 2. Chlorination at C-2 will not create any chiral centers (so 1 here). Chlorination at C-3 will make C-3 a chiral center (2 here) and chlorination at C-4 will not make any chiral centers (1 more here). So a total of 6. (But all 6 are not stereoisomers of each other I guess since they have different arrangements of bonds. I think the question might have been "how many isomers result, counting stereoisomers separately?" no?

 

[alanan84]

6 is correct. chlorination at C-1 makes C-2 a chiral center, so that will give 2. Chlorination at C-2 will not create any chiral centers (so 1 here). Chlorination at C-3 will make C-3 a chiral center (2 here) and chlorination at C-4 will not make any chiral centers (1 more here). So a total of 6. (But all 6 are not stereoisomers of each other I guess since they have different arrangements of bonds. I think the question might have been "how many isomers result, counting stereoisomers separately?" no?

Yeah that's right!

 

[omgdats]

thanks! i didnt realize that C2 became a chiral carbon...