Pinacol Rearrangement of asymmetrical diol

  • Context: Chemistry 
  • Thread starter Thread starter qkfqkekr
  • Start date Start date
Click For Summary
SUMMARY

The discussion centers on the pinacol rearrangement of 1,1-diphenylethane-1,2-diol. The participant correctly identifies that protonation of the hydroxyl group at carbon 1 leads to the formation of a stable tertiary carbocation. However, they also recognize that for the rearrangement to occur, the hydroxyl group on carbon 2 must be involved in the process. This highlights the importance of understanding the stability of carbocations in determining the mechanism of rearrangement.

PREREQUISITES
  • Understanding of pinacol rearrangement mechanisms
  • Familiarity with carbocation stability and protonation
  • Knowledge of 1,1-diphenylethane-1,2-diol structure
  • Basic organic chemistry reaction mechanisms
NEXT STEPS
  • Study the detailed mechanism of pinacol rearrangement
  • Explore the stability of different types of carbocations
  • Investigate the role of protonation in organic reactions
  • Learn about related rearrangement reactions in organic chemistry
USEFUL FOR

Organic chemistry students, researchers in chemical synthesis, and educators teaching reaction mechanisms will benefit from this discussion.

qkfqkekr
Messages
1
Reaction score
0
Homework Statement
write down the mechanism of pinacol arrangement of the following diols
Relevant Equations
none
I have a question for the first part a), pinacol rearrangement of 1,1-diphenylethane-1,2-diol (did I name that right..?).
How would you know if protonation takes place on the hydroxyl molecule attached to carbon 1 or carbon 2?
My guess is that the hydroxyl group at carbon 1 would be protonated, since leaving of the hydroxyl group (as water) will yield tertiary carbocation, which is stable.
Is this approach correct?
1628247401136.png



Thank you for your help!
 
Physics news on Phys.org
qkfqkekr said:
Homework Statement:: write down the mechanism of pinacol arrangement of the following diols
Relevant Equations:: none

I have a question for the first part a), pinacol rearrangement of 1,1-diphenylethane-1,2-diol (did I name that right..?).
How would you know if protonation takes place on the hydroxyl molecule attached to carbon 1 or carbon 2?
My guess is that the hydroxyl group at carbon 1 would be protonated, since leaving of the hydroxyl group (as water) will yield tertiary carbocation, which is stable.
Is this approach correct?
View attachment 287170


Thank you for your help!
If the hydroxyl group at carbon 1 was protonated, then which group would undergo rearrangement for the piñacolada to become piñacologne? I believe it needs to be the hydroxyl group on carbon 2.
 

Similar threads

  • · Replies 2 ·
Replies
2
Views
2K
  • · Replies 1 ·
Replies
1
Views
6K
Replies
1
Views
6K
  • · Replies 1 ·
Replies
1
Views
5K
  • · Replies 5 ·
Replies
5
Views
4K
  • · Replies 11 ·
Replies
11
Views
20K
  • · Replies 1 ·
Replies
1
Views
4K
  • · Replies 3 ·
Replies
3
Views
3K
  • · Replies 8 ·
Replies
8
Views
945
  • · Replies 8 ·
Replies
8
Views
4K