1,2-Alkyl shifts vs. hydride shifts

  • Thread starter Thread starter CrimpJiggler
  • Start date Start date
AI Thread Summary
In carbocation rearrangements, alkyl shifts typically occur when the adjacent carbon is tertiary, as this allows for the formation of a more stable carbocation. Hydride shifts are not possible from tertiary carbons due to the absence of hydrogen atoms. The discussion emphasizes the importance of evaluating the stability of the carbocation formed after potential shifts. If an alkyl shift can yield a more stable tertiary carbocation from a secondary one, it should be prioritized. If neither alkyl nor hydride shifts are feasible, the original carbocation should be retained. The effectiveness of this approach is noted to be applicable in most cases, although specific examples of simultaneous hydride and alkyl shifts leading to the same carbocation are not readily identified.
CrimpJiggler
Messages
141
Reaction score
1
In carbocation rearrangements, do alkyl shifts only occur when the carbon adjacent the carbocation is a tertiary carbon and thus, a hydride shift cannot occur (because there is no hydrogen attached to the tertiary carbon)?
 
Chemistry news on Phys.org
im not very sure regarding all reactions but i always check the carbocation formed in any step...if alkyl shift is possible and gives a more stable product,say tertiary from secondary,then form this new carcocation,else try for hydride shift,if possible...else use the original carbocation
 
I was going to try and give an example in which a hydride shift and alkyl shift yield the same carbocation but I can't think of any. So it seems like your approach should be effective in the majority (if not all) of cases.
 
It seems like a simple enough question: what is the solubility of epsom salt in water at 20°C? A graph or table showing how it varies with temperature would be a bonus. But upon searching the internet I have been unable to determine this with confidence. Wikipedia gives the value of 113g/100ml. But other sources disagree and I can't find a definitive source for the information. I even asked chatgpt but it couldn't be sure either. I thought, naively, that this would be easy to look up without...
I was introduced to the Octet Rule recently and make me wonder, why does 8 valence electrons or a full p orbital always make an element inert? What is so special with a full p orbital? Like take Calcium for an example, its outer orbital is filled but its only the s orbital thats filled so its still reactive not so much as the Alkaline metals but still pretty reactive. Can someone explain it to me? Thanks!!
Back
Top