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

  • Thread starter Thread starter baldbrain
  • Start date Start date
  • Tags Tags
    Compounds Product
Click For Summary
The discussion centers on the mechanisms of SN1 and SN2 reactions and how they can yield the same products under certain conditions. It highlights the importance of the geometry of the carbon center, noting that SN2 allows only backside attacks, while SN1 involves a carbocation intermediate that can rearrange. The participants debate whether specific compounds can produce identical products from both mechanisms, with a focus on stereogenic centers and racemic mixtures. Ultimately, it is concluded that if a compound starts as a racemic mixture, both mechanisms can yield the same product, while rearrangements and stereochemistry play crucial roles in determining the outcomes. The conversation emphasizes the need for clarity in understanding these mechanisms to avoid confusion during examinations.
  • #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).
 
Physics news on Phys.org
  • #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?
 

Similar threads

  • · Replies 2 ·
Replies
2
Views
3K
  • · Replies 1 ·
Replies
1
Views
3K
  • · Replies 3 ·
Replies
3
Views
8K
  • · Replies 1 ·
Replies
1
Views
3K
Replies
1
Views
2K
  • · Replies 10 ·
Replies
10
Views
3K
Replies
1
Views
1K
  • · Replies 5 ·
Replies
5
Views
3K
  • · Replies 1 ·
Replies
1
Views
2K
  • · Replies 6 ·
Replies
6
Views
3K