Checking Ochem Reaction Validity: 1-Methyl-1-Cyclohexanol with HBr and EtO-/EtOH

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SUMMARY

The discussion centers on the reaction of 1-methyl-1-cyclohexanol with HBr and subsequent treatment with EtO-/EtOH. The expected product from the initial reaction is 1-bromo-1-methylcyclohexane, which can then undergo elimination to form 1-methyl-1-cyclohexene. The professor's alternative method involves using sulfuric acid to generate a carbocation, which also leads to the same product. Key considerations include the stability of the carbocation and the trans elimination mechanism.

PREREQUISITES
  • Understanding of organic reaction mechanisms, specifically nucleophilic substitutions and eliminations.
  • Familiarity with carbocation stability and rearrangements.
  • Knowledge of the role of acids in organic reactions, particularly sulfuric acid.
  • Experience with reaction products and stereochemistry in organic chemistry.
NEXT STEPS
  • Study the mechanism of nucleophilic substitution reactions involving HBr.
  • Learn about carbocation rearrangements and their implications in organic synthesis.
  • Research elimination reactions and the significance of stereochemistry in product formation.
  • Explore the role of sulfuric acid in generating reactive intermediates in organic reactions.
USEFUL FOR

This discussion is beneficial for organic chemistry students, educators, and researchers interested in reaction mechanisms and product formation in organic synthesis.

tandoorichicken
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I did this problem a little differently than my professor, so I need someone to check if it is valid.

Let's start with 1-methyl-1-cyclohexanol. If I react this with HBr, I should get 1-bromo-1-methylcyclohexane. And if I then react this with EtO-/EtOH, I should get 1-methyl-1-cyclohexene, right?

My professor wrote a reaction with sulfuric acid to give a carbocation that reacted with water to give the same product.
 
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You are going to need to consider whether the carbocation site would transfer itself in this case, also, remember that the elimination mechanism takes place in trans.
 

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