Organic chemistry addition reaction

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SUMMARY

The discussion centers on the addition reaction in organic chemistry, specifically regarding the stability of carbocations during a reaction. The participant initially considered a hydride shift for better carbocation stability but opted for an alkyl shift due to time constraints during an exam. Clarification was provided that carbocations are not tetrahedral, and the expected product involves a migration of the positive charge to the nearest tertiary carbon, resulting in a tetra-substituted alkene.

PREREQUISITES
  • Understanding of carbocation stability and rearrangements
  • Knowledge of hydride and alkyl shifts in organic reactions
  • Familiarity with tetra-substituted alkenes
  • Basic principles of addition reactions in organic chemistry
NEXT STEPS
  • Study the mechanisms of carbocation rearrangements in organic reactions
  • Learn about the stability of different types of alkenes and their formation
  • Explore examples of hydride and alkyl shifts in various organic reactions
  • Investigate the role of sterics and electronics in determining reaction pathways
USEFUL FOR

Students studying organic chemistry, particularly those preparing for exams involving reaction mechanisms and carbocation stability.

Mdhiggenz
Messages
324
Reaction score
1

Homework Statement



nmat0l.jpg



Number 8 is the one I was unsure of in my exam.

I know a hydride shift would give it a better carbocation, however it was not tetra hedral, so I panicked, and quickly did a alkyl shift, it worked out on the exam, but I was on the verge of running out of time so I did not really check.

What do you think?



Homework Equations





The Attempt at a Solution

 
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Mdhiggenz said:

Homework Statement



nmat0l.jpg
Number 8 is the one I was unsure of in my exam.

I know a hydride shift would give it a better carbocation, however it was not tetra hedral, so I panicked, and quickly did a alkyl shift, it worked out on the exam, but I was on the verge of running out of time so I did not really check.

What do you think?

Homework Equations


The Attempt at a Solution


I do not understand what you mean by "it was not tetrahedral", are you talking about the carbocation? If so, carbocations are never tetrahedral.

I am not sure what could be the product but I think the positive charge migrates to the nearest tertiary carbon and give a tetra substituted alkene.
 
Mmdhiggenz

The picture does seem to show the necessary hydride shift ( probably a correction by your professor)
 

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