How can any of these compounds give same SN1 & SN2 product?

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Discussion Overview

The discussion revolves around the mechanisms of SN1 and SN2 reactions and how certain compounds can yield the same products through both pathways. Participants explore the influence of molecular geometry, stereochemistry, and the presence of π bonds on the reaction mechanisms and outcomes.

Discussion Character

  • Debate/contested
  • Technical explanation
  • Conceptual clarification

Main Points Raised

  • Some participants question the role of hindrance caused by π bonds in affecting the SN2 mechanism compared to SN1.
  • There is a discussion on the geometries of intermediates in SN1 (carbocation, trigonal planar) and SN2 (transition state, coplanar arrangement) reactions.
  • Some participants suggest that the same products from SN1 and SN2 are possible if the substitution center is not stereogenic.
  • Others argue that the presence of a racemic mixture in the starting material is crucial for the correctness of the proposed answers.
  • There is a debate on whether certain compounds can lead to achiral products due to rearrangements in the carbocation intermediates.
  • Some participants express uncertainty about the conditions under which racemization or rearrangement is the deciding factor in product formation.

Areas of Agreement / Disagreement

Participants express differing views on the influence of stereogenic centers and the role of π bonds in determining the products of SN1 and SN2 reactions. The discussion remains unresolved, with multiple competing perspectives on the mechanisms and outcomes.

Contextual Notes

There are limitations in the assumptions made regarding the stereogenic nature of substitution centers and the implications of carbocation stability on the reaction pathways. The discussion also highlights the complexity of determining the dominant mechanism based on molecular structure.

  • #31
HPPAS said:
But is there a general rule so as to decide which factor dominates under what conditions?
It's not a matter of one factor dominating over another (at least not for this question). Rearrangements will happen, and stereochemical effects will happen. I unfortunately didn't think of rearrangements when I initially answered your question, but Ygggdrasil did, and his answer was therefore on the money. If you consider only rearrangements, then c will be the correct answer. If you consider rearrangements and stereochemistry, c is still correct, assuming that you start with a racemic mixture of c. If you assume that you start with one enantiomer of c, then there is no correct answer (SN1 and SN2 give different compunds in every case).
 
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  • #32
TeethWhitener said:
It's not a matter of one factor dominating over another (at least not for this question). Rearrangements will happen, and stereochemical effects will happen. I unfortunately didn't think of rearrangements when I initially answered your question, but Ygggdrasil did, and his answer was therefore on the money. If you consider only rearrangements, then c will be the correct answer. If you consider rearrangements and stereochemistry, c is still correct, assuming that you start with a racemic mixture of c. If you assume that you start with one enantiomer of c, then there is no correct answer (SN1 and SN2 give different compunds in every case).
Oh. Yes, that last bit was very helpful thanks to @Ygggdrasil .
All my concepts are quite clear, but I still **** up during exams (probably due to haste). I also solve a lot of problems, I can get them quicker when there's no time limit.
Sometimes, the opposite happens. I get the good problems, and **** up the easy ones. Can you give me some advice regarding this?
 

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