Sciencemadness Discussion Board

Attempting to self-teach a bit of organic chemistry this summer.

Velzee - 18-6-2016 at 15:34

Hey SM,

I'm attempting to self-teach myself about a bit of Organic Chemistry. But I would to go about doing so by forcing myself to make use of one of my reagents that I've yet to use for anything—1L of 1,3-propanediol.

Now, before I go any further, I should tell you approximately about how much I know of organic chemistry:

I know essentially as much, but probably less than what this packet contains(I received it in my normal chemistry class—the X's and "Organic Reactions" (except "A") mark the topics that we skipped):
https://drive.google.com/open?id=0B964AW0fUdkLMlQyaHAydU9kT2...

With that being said, know how to draw most compounds except everything beyond that pack (excluding the X'd items).

I drew a molecule of 1,3-propanediol, and read up a little on diols. I found that diols are capable of being converted to cyclic ethers(I don't really understand how cyclic affects anything), ethers, and esters. Therefore, I'd like to do just that—convert 1,3-propanediol to an ether, possibly methyl ethyl ether, with water as a side product.

But I'm just a beginner—a novice—but I'm willing to accept any help at all, including a place to start.

Thank you in advance!

—Elyjah

Metacelsus - 18-6-2016 at 16:44

How would you get methyl ethyl ether from propanediol? It doesn't make sense.

You could try reacting it with formaldehyde to form 1,3-dioxane (a cyclic acetal).

Crowfjord - 18-6-2016 at 17:33

Maybe Velzee means adding a methyl to one oxygen and an ethyl to the other? If that were the case, that would be pretty difficult, especially for a beginner. Doing just methyl or ethyl on both sides would probably be doable, using the corresponding alcohol and sulfuric acid.

Another use for 1,3-propanediol would be oxidation to malonic acid. There are multiple methods on the forum, I think, one of them using nitric acid as the oxidant.

Velzee - 18-6-2016 at 18:09

Quote: Originally posted by Crowfjord  
Maybe Velzee means adding a methyl to one oxygen and an ethyl to the other? If that were the case, that would be pretty difficult, especially for a beginner. Doing just methyl or ethyl on both sides would probably be doable, using the corresponding alcohol and sulfuric acid.

Another use for 1,3-propanediol would be oxidation to malonic acid. There are multiple methods on the forum, I think, one of them using nitric acid as the oxidant.


Yes, I was thinking about your second suggestion—having a methyl and ethyl on either side—how would I go about performing such a process?

[Edited on 6/19/2016 by Velzee]

Crowfjord - 18-6-2016 at 18:13

See here, for example.

Velzee - 18-6-2016 at 18:18

Okay. I'm going to need to obtain some funds before attempting that. I haven't been able to purchase HNO3 nor the equipment used to handle making it. Can the reaction be performed without using HNO3—using another oxidizing agent perhaps?

Crowfjord - 18-6-2016 at 18:33

Potassium permanganate perhaps? Lots of ways out there, not hard to find with some searching.

DraconicAcid - 18-6-2016 at 22:13

Bleach might work.