Oxidation of alkene followed by Cu, heat

In summary, the oxidation of alkenes in the presence of copper (Cu) and heat typically leads to the formation of carbonyl compounds, such as aldehydes or ketones. This reaction involves the addition of oxygen and results in the cleavage of the double bond of the alkene, facilitating further transformation of the resulting intermediates under the catalytic influence of copper and elevated temperatures.
  • #1
Sat-P
53
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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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  • #2
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).
 

FAQ: Oxidation of alkene followed by Cu, heat

What is the general reaction mechanism for the oxidation of alkenes followed by copper and heat?

The oxidation of alkenes typically involves the addition of oxygen or an oxidizing agent, leading to the formation of various products such as alcohols, ketones, or carboxylic acids. When copper is introduced and heat is applied, it can facilitate further oxidation or rearrangement of the initial products, often resulting in the formation of aldehydes or acids, depending on the starting alkene and reaction conditions.

What role does copper play in the oxidation of alkenes?

Copper acts as a catalyst in the oxidation reaction. It can facilitate the transfer of electrons and stabilize intermediates formed during the reaction. The heat enhances the reaction rate and can help overcome activation energy barriers, leading to more efficient oxidation of the alkene.

What are the common products formed from the oxidation of alkenes with copper and heat?

The common products can vary based on the structure of the alkene and the specific reaction conditions. Generally, the oxidation of alkenes can yield alcohols, aldehydes, ketones, or carboxylic acids. In some cases, further oxidation can lead to the formation of carbon dioxide and water, especially if the alkene is fully oxidized.

Are there specific types of alkenes that react better with copper and heat during oxidation?

Yes, more substituted alkenes often react more readily due to their increased stability and lower activation energy for oxidation. Additionally, alkenes with electron-donating groups or those that can stabilize positive charges during the reaction may also show enhanced reactivity when treated with copper and heat.

What safety precautions should be taken when performing oxidation reactions involving copper and heat?

When conducting oxidation reactions, it is important to work in a well-ventilated area or under a fume hood to avoid inhaling harmful vapors. Proper personal protective equipment (PPE) such as gloves, goggles, and lab coats should be worn. Additionally, care should be taken when handling hot equipment and reactive chemicals to prevent burns or accidents.

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