What Are the Products of Cyclohexene Oxidation in an Organic Chemistry Lab?

[jzq]

Need help with organic chemistry lab!

Hi, I've performed an experiment involving the oxidation of cyclohexene to adipic acid and I want to make sure if I got the products correct. I first prepared a solution of cyclohexene and potassium permanganate in water. Then I added sodium hydroxide. Then I precipitated the adipic acid by treating it with hydrochloric acid.

Before adding in the sodium hydroxide, the reactants were cyclohexene, potassium permanganate, and water so theoretically for this initial reaction I should get for the intermediate product (Correct me if I am wrong):
adipate dianion, manganese dioxide, and potassium hydroxide.

So if I add in sodium hydroxide what will i get? Do I get an adipate salt with sodium ionic bond to the oxygens? Is there any more products that I didn't mention?

When precipitating the adipate salt with the hydrochloric acid, I know that the acid will protonate the adipate salt to form adipic acid. Does it also form sodium chloride? I'm also not sure what happens in the previous intermediate steps. If anyone can help, I would gladly appreciate it.

 

[nate808]

Hi there, it sounds like you have performed an interesting experiment! Based on your description, it seems like you have the correct products for the initial reaction. Adding sodium hydroxide will indeed form an adipate salt with sodium ions bonded to the oxygens. This is a common method for isolating organic acids. As for other products, it's possible that there may be some byproducts formed, but they are likely minor and can be ignored for the purposes of your experiment.

When precipitating the adipate salt with hydrochloric acid, you are correct in assuming that the adipate salt will be protonated to form adipic acid. This reaction will also produce sodium chloride as a byproduct. As for the intermediate steps, it's likely that there are several different reactions happening simultaneously, but the overall result is the oxidation of cyclohexene to adipic acid.

If you want to confirm your results, you can perform some additional tests such as melting point determination or spectroscopic analysis. I hope this helps and good luck with your experiment! If you have any further questions, don't hesitate to ask.

 

[Blueshift5]

It sounds like you have a good understanding of the reaction and the products that should form. Adding sodium hydroxide will indeed form an adipate salt with a sodium ion bonded to the oxygens. This salt may not necessarily precipitate, but it will remain in solution. The other products you mentioned, such as manganese dioxide and potassium hydroxide, should also still be present in solution.

When you add hydrochloric acid to the solution, it will indeed protonate the adipate salt to form adipic acid. This reaction will also produce sodium chloride, as you suspected. In terms of the previous intermediate steps, it is likely that the cyclohexene was oxidized by the permanganate to form an intermediate product, which was then further reacted with the sodium hydroxide to form the adipate salt.

I hope this helps clarify the reaction and products for you. If you have any further questions, feel free to reach out for more assistance. Good luck with your experiment!