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Question

(1S,2R,4R)-1-chloro-2,4-dimethylcyclohexane

Total number of SN1 products of given compound are

A) $3$

B) $4$

C) $5$

D) $6$

Answer

(C) $5$

My attempt

I can find only $4$ products. The two stereoisomers formed from the carbocation, when chlorine leaves, and two stereoisomers formed when the hydrogen from the neighbouring carbon centre migrates (i.e. rearrangement occurs) and nucleophilic attack takes place from both sides.

I still am unable to find the fifth product. Moreover, I don't suppose the $\ce{-CH3}$ opposite to the point where the carbocation forms can interfere with the product. What would be the fifth product?

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  • $\begingroup$ chemistry.meta.stackexchange.com/questions/4808/…. When asking problem statements, could you try to conform to this template? You seem to be someone who would stick through SE for an extended period of time and we would be glad to keep it that way $\endgroup$
    – Safdar Faisal
    Jul 30, 2020 at 12:58
  • $\begingroup$ @Safdar I started actively today in this forum. Hence I am unaware about the etiquette. I shall keep the code of questioning in mind. $\endgroup$
    – Solid - NMR
    Jul 30, 2020 at 13:09
  • $\begingroup$ For formatting, See here and here. For a more detailed MathJax guide, look here, minor other details $\endgroup$
    – Safdar Faisal
    Jul 30, 2020 at 13:10
  • $\begingroup$ Is there no other information given in this question? $\endgroup$
    – Safdar Faisal
    Jul 30, 2020 at 13:16
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    $\begingroup$ A very weird proposition, a hydride shift to the other side since the number of alpha hydrogens increases from 3 to 4, the other shift is more stable since it goes from 3 to 7, but still is possible. This makes the answer 6 though. @YusufHasan $\endgroup$
    – Safdar Faisal
    Jul 30, 2020 at 15:25

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