orgo question

[RUpremed]

Hi all,

So i'm going thru the DAT destroyer, and there is one question which I don't understand...

What I don't understand is, why is the double bond formed at the least substituted carbon? Wouldn't you consider the peroxide only after the double bond is formed?

Thanks.

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[kevinrho]

#177? well its #177 2k10 edition. I think what it is supposed to be is 1. SOCl2, 2. (CH3)3CO-K+/CH3)3COH 3. HBr/ROOR

someone can correct me if i'm wrong, but based on my understanding when adding 2. (CH3)3CO-K+/CH3)3COH, it is a bulky base therefore causes steric hindrance leading to the formation of the double bond on the least substituted carbon.

 

[anonymuz]

1. OH gets replaced by Cl
2. Bulky base removes H at C1 and Cl at C2 making a double bond between C1 and C2.
3. HBr with ROOR adds antimarkonikov, hence your answer

 

[rnbaxter]

Hi all,

So i'm going thru the DAT destroyer, and there is one question which I don't understand...

What I don't understand is, why is the double bond formed at the least substituted carbon? Wouldn't you consider the peroxide only after the double bond is formed?

Thanks.

Step 1) you form your alkyl chloride
Step 2) this is a bulky nucleophile so through your E2 rxn it does not follow the Z guy's rule. Therefore, removing your less substituted B-hydrogen. If you had a nucleophile like methoxide you would be correct.
Step 3) antimark addition

 

[chromosome21]

1. Oh gets replaced by cl
2. Bulky base removes h at c1 and cl at c2 making a double bond between c1 and c2.
3. Hbr with roor adds antimarkonikov, hence your answer

+1