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

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This discussion focuses on the mechanisms of SN1 and SN2 reactions, specifically addressing how certain compounds can yield the same products despite differing mechanisms. The participants clarify that the geometry of the carbon center plays a crucial role, with SN1 involving a trigonal planar carbocation and SN2 requiring a coplanar transition state. The consensus is that compounds with non-stereogenic centers, particularly compound (b), can produce identical products from both mechanisms, while compound (c) may yield the same result only if it is a racemic mixture. The importance of carbocation rearrangement and stereochemical considerations is emphasized throughout the conversation.

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  • #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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