Dehydration Problem: Solving for the Location of a Double Bond in a Carbocation

Click For Summary

Discussion Overview

The discussion revolves around a homework problem related to the formation of a double bond in a carbocation during a dehydration reaction. Participants explore the implications of Zaitsev's rule and the structural considerations of the molecule in question.

Discussion Character

  • Homework-related
  • Debate/contested
  • Conceptual clarification

Main Points Raised

  • One participant expresses uncertainty about where the double bond will form in the carbocation, noting that two positions appear equivalent.
  • Another participant suggests looking up Zaitsev's rule, implying it may provide insight into the double bond formation.
  • A subsequent reply acknowledges the application of Zaitsev's rule but points out that both positions are equally substituted, raising a question about the expected outcome.
  • Another participant proposes an alternative approach by suggesting the drawing of the molecule in its enol form, indicating a different pathway to understand the reaction mechanism.

Areas of Agreement / Disagreement

Participants do not reach a consensus on the location of the double bond formation, with multiple competing views and approaches presented throughout the discussion.

Contextual Notes

Participants discuss the implications of structural features and rules like Zaitsev's without resolving the uncertainty regarding the double bond's location. The discussion reflects differing interpretations of the reaction mechanism.

vijayramakrishnan
Messages
90
Reaction score
0

Homework Statement


Please see question number 31

http://cms.fiitjee.co/Resources/DownloadCentre/Document_Pdf_183.pdf

Homework Equations


none

The Attempt at a Solution



i got up to second step in the solution(scroll downwards) but in the last step a carbocation is formed and double bond can be formed in two places b and a. they seem to be equivalent places,i don't know where the double bond will be formed.
 
Physics news on Phys.org
Look up Zaitsev's rule.
 
TeethWhitener said:
Look up Zaitsev's rule.
but here both are equally substituted sir
 
Ah, I see now. You're wondering why the double bond doesn't form between the two bridgehead carbons? This might be because you're envisioning protonating the OH group at the bridgehead carbon and eliminating a water to give a tertiary carbocation. In this case however, you have to do something a little different. Start by drawing the molecule in the enol form. Can you get it from here?
 

Similar threads

  • · Replies 1 ·
Replies
1
Views
2K
  • · Replies 1 ·
Replies
1
Views
2K
  • · Replies 5 ·
Replies
5
Views
5K
  • · Replies 1 ·
Replies
1
Views
6K
  • · Replies 1 ·
Replies
1
Views
6K
Replies
10
Views
6K
  • · Replies 2 ·
Replies
2
Views
3K
Replies
1
Views
2K
  • · Replies 21 ·
Replies
21
Views
6K
Replies
5
Views
9K