1,2-Alkyl shifts vs. hydride shifts

  • Thread starter Thread starter CrimpJiggler
  • Start date Start date
Join the discussion
Registration is free. Start your own thread to ask a follow-up.
2 replies · 5K views
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.