Oxidation of alkene followed by Cu, heat

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SUMMARY

The discussion centers on the oxidation of alkenes using copper and heat, specifically addressing the confusion surrounding Markovnikov's rule and the resulting products. The correct application of Markovnikov addition places the hydroxyl group on the more substituted carbon, resulting in a tertiary alcohol. The subsequent exposure of this tertiary alcohol to copper and heat leads to dehydration, producing an alkene in accordance with Zaitsev's rule. The initial misunderstanding stemmed from a misinterpretation of the addition process.

PREREQUISITES
  • Understanding of Markovnikov's rule in organic chemistry
  • Familiarity with oxymercuration/reduction reactions
  • Knowledge of dehydration reactions and Zaitsev's rule
  • Basic principles of alkene and alcohol reactivity
NEXT STEPS
  • Study the mechanisms of oxymercuration and reduction reactions
  • Learn about the dehydration of alcohols and the role of copper as a catalyst
  • Explore detailed examples of Markovnikov and anti-Markovnikov additions
  • Investigate the applications of Zaitsev's rule in synthetic organic chemistry
USEFUL FOR

Chemistry students, organic chemists, and anyone interested in reaction mechanisms involving alkenes and alcohols.

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Messages
53
Reaction score
4
Homework Statement
Find product B
Relevant Equations
None
IMG_20240725_221157.jpg

The answer I am getting is A but the answer given is D. I don't know why D because this is what I did. First I opened the alkene and then added OH on the less substituted carbon( Markonikov addition) and we know that Cu, Heat turns 3° alcohol to alkene so then I got an alkene.
Did I do something wrong or the answer is incorrect?
 
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Wow that question is written in an incredibly confusing way. I think you’re right, except for the part where you say Markovnikov addition puts the hydroxyl on the less substituted carbon. But I think that’s just a typo on your part, as you clearly understand in the next sentence that the product of the oxymercuration/reduction is a tertiary alcohol (the more substituted carbon, thus following Markovnikov’s rule). Other than that, yes, exposure of a tert alcohol to copper and heat should dehydrate the compound to an alkene (following Zaitsev’s rule).
 

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