Sciencemadness Discussion Board

Acetone - Acids reaction

khourygeo78 - 27-1-2016 at 11:57

Anyone has any idea about these reactions? and what do they yield? Or if there is anything readable on the web that can answer my question? I tried searching but nothing unfortunately :(
Thanks

Acetone + Sulfuric acid

Acetone + nitric acid

Acetone + hydrochloric acid

Acetone + citric acid

Acetone + acetic acid

gdflp - 27-1-2016 at 12:19

Look up the acid-catalyzed aldol condensation. I'm not sure off the top of my head if those organic acids are strong enough, but the mineral acids certainly are. Sorry, I don't have time to explain further right now.

DraconicAcid - 27-1-2016 at 12:29

Sulphuric acid, I believe, will react with acetone to give trimethylbenzene.

Detonationology - 27-1-2016 at 12:33

Acids do not "react" with ketones to produce new product to my knowledge. However, since acids have H+ ions, they are able to protonate the carbonyl, effectively breaking the double bond as an intermediate. At this step, another compound is able to step in to fill the void made by the protonation. The first example that comes to mind is the synthesis of TATP.

I am by no means knowledgable in organic; I'm simply a novice.

Figure-7-Mechanism-for-the-synthesis-of-TATP-and-DADP.jpg - 39kB

blogfast25 - 27-1-2016 at 13:07

Quote: Originally posted by Detonationology  


I am by no means knowledgable in organic; I'm simply a novice.

D'you have a reference for that scheme?

Detonationology - 27-1-2016 at 13:22

Quote: Originally posted by blogfast25  
D'you have a reference for that scheme?

Of course!
Factors Influencing Triacetone Triperoxide (TATP) and Diacetone Diperoxide (DADP) Formation: Part 2

[edit] Idk why the hot link won't work when you click on it, you have to delete SciMad from the beginning

[Edited on 1-27-2016 by Detonationology]

fluorescence - 27-1-2016 at 13:37

Acetone + Acid will yield in first a yellow-brown solution which will precipitate some black stuff and eventually if you wait long enough for the Acetone to evaporate you will get a red-black oil. I tried that myself a few times to see what happens and it always ended in a polymer formed by Aldol reactions.

Detonationology - 27-1-2016 at 14:03

Quote: Originally posted by fluorescence  
Acetone + Acid

What acid are you referring to?

PHILOU Zrealone - 27-1-2016 at 15:54

Conc H2SO4 is able to polymerise aceton into 1,3,5-trimethylbenzene (mesitylene).

Conc HCl will make lower polymer like phoron.

Conc HNO3 will lead you to a really vigorous runnaway (the all batch will boil at once in nxoy fumes with a short delay time depending on initial temperature) and various undefined nitro/nitroso/oxydation resulting compounds.

Citric acid will yield nothing but the mix, just like acetic acid...

[Edited on 27-1-2016 by PHILOU Zrealone]

Amos - 27-1-2016 at 17:58

Detonationology, all of the reaction mechanisms in that diagram you posted are only possible if hydrogen peroxide is present.

Detonationology - 27-1-2016 at 18:06

Quote: Originally posted by Amos  
Detonationology, all of the reaction mechanisms in that diagram you posted are only possible if hydrogen peroxide is present.

Hmm... is the carbonyl not protonated by the acid regardless?

blogfast25 - 27-1-2016 at 18:39

@detonationology:

Please be more careful when citing, in the future. You pulled that graphic seriously out of context, as Amos showed. :o

At LEAST browse the sources you are quoting.

[Edited on 28-1-2016 by blogfast25]

Detonationology - 27-1-2016 at 18:42

How so? Please explain in detail.


I can accept being incorrect about my original statement, just tell me why it is wrong or irrelevant.

We stand at the "Contradiction" level of "the pyramid of debate: "states the opposing case with little or no supporting evidence."

[Edited on 1-28-2016 by Detonationology]

Etaoin Shrdlu - 27-1-2016 at 19:09

Eh, I really don't see hydrogen peroxide being "required" for Detonationology's point. That was the same basic mechanism as acid-catalyzed aldol condensation or hemiacetal formation, just a different nucleophile.

That reaction diagram might have had different reactants, but it still shows how acids usually tend to protonate the carbonyl to facilitate the attack of a nucleophile rather than incorporating into the final product. In this case we're looking at self-condensation where the enol form of acetone is the nucleophile.

blogfast25 - 28-1-2016 at 01:37

Quote: Originally posted by Etaoin Shrdlu  
Eh, I really don't see hydrogen peroxide being "required" for Detonationology's point. That was the same basic mechanism as acid-catalyzed aldol condensation or hemiacetal formation, just a different nucleophile.

That reaction diagram might have had different reactants, but it still shows how acids usually tend to protonate the carbonyl to facilitate the attack of a nucleophile rather than incorporating into the final product. In this case we're looking at self-condensation where the enol form of acetone is the nucleophile.


Maybe you should actually read it? W/o hydrogen peroxide NONE of the listed structures is possible. Hardly relevant to the OP's question though...

Detonationology - 28-1-2016 at 04:36

Quote: Originally posted by blogfast25  
Quote: Originally posted by Etaoin Shrdlu  
Eh, I really don't see hydrogen peroxide being "required" for Detonationology's point. That was the same basic mechanism as acid-catalyzed aldol condensation or hemiacetal formation, just a different nucleophile.

That reaction diagram might have had different reactants, but it still shows how acids usually tend to protonate the carbonyl to facilitate the attack of a nucleophile rather than incorporating into the final product. In this case we're looking at self-condensation where the enol form of acetone is the nucleophile.


Maybe you should actually read it? W/o hydrogen peroxide NONE of the listed structures is possible. Hardly relevant to the OP's question though...

"hardly relevant." Would you remind me what DOES occur when, say HCl, is combined with acetone? Please explain in great detail...

Etaoin Shrdlu - 28-1-2016 at 05:24

Quote: Originally posted by blogfast25  
Quote: Originally posted by Etaoin Shrdlu  
Eh, I really don't see hydrogen peroxide being "required" for Detonationology's point. That was the same basic mechanism as acid-catalyzed aldol condensation or hemiacetal formation, just a different nucleophile.

That reaction diagram might have had different reactants, but it still shows how acids usually tend to protonate the carbonyl to facilitate the attack of a nucleophile rather than incorporating into the final product. In this case we're looking at self-condensation where the enol form of acetone is the nucleophile.


Maybe you should actually read it? W/o hydrogen peroxide NONE of the listed structures is possible. Hardly relevant to the OP's question though...

Maybe you should actually read his post.

EDIT: Detonationology only ever proposed this as an example of the mechanism. "However, since acids have H+ ions, they are able to protonate the carbonyl, effectively breaking the double bond as an intermediate. At this step, another compound is able to step in to fill the void made by the protonation."

It was a perfectly good example of the mechanism. Stop grousing that the nucleophile is different.

[Edited on 1-28-2016 by Etaoin Shrdlu]

blogfast25 - 28-1-2016 at 07:23

Grousing??? LOL:D

Detonationology - 28-1-2016 at 09:04

Lol. That sure is one humble way of admit to being incorrect.

khourygeo78 - 28-1-2016 at 11:45

Quote: Originally posted by fluorescence  
Acetone + Acid will yield in first a yellow-brown solution which will precipitate some black stuff and eventually if you wait long enough for the Acetone to evaporate you will get a red-black oil. I tried that myself a few times to see what happens and it always ended in a polymer formed by Aldol reactions.


Interesting! Do you remember the smell of the red-black oil?
And didnt the acetone react with the acid to make a volatile compound (non oily). This can be perceived by smell&speed of evaporation.

khourygeo78 - 28-1-2016 at 11:46

Quote: Originally posted by PHILOU Zrealone  
Conc H2SO4 is able to polymerise aceton into 1,3,5-trimethylbenzene (mesitylene).

Conc HCl will make lower polymer like phoron.

Conc HNO3 will lead you to a really vigorous runnaway (the all batch will boil at once in nxoy fumes with a short delay time depending on initial temperature) and various undefined nitro/nitroso/oxydation resulting compounds.

Citric acid will yield nothing but the mix, just like acetic acid...

[Edited on 27-1-2016 by PHILOU Zrealone]


thanks. i just didnt understand what you meant by
"Conc HCl will make lower polymer like phoron". What does phoron mean here

The Volatile Chemist - 28-1-2016 at 13:52

Phoron's just the name of a polymer.

Does anyone have a source for:
Quote:
Conc H2SO4 is able to polymerise aceton into 1,3,5-trimethylbenzene (mesitylene).

Of course it seems that other users weren't able to perform this anyways.

DraconicAcid - 28-1-2016 at 14:08

Quote: Originally posted by The Volatile Chemist  

Does anyone have a source for:
Quote:
Conc H2SO4 is able to polymerise aceton into 1,3,5-trimethylbenzene (mesitylene).

Of course it seems that other users weren't able to perform this anyways.


I know which book I remember reading it in, but don't have it handy.

But it's here: http://www.orgsyn.org/demo.aspx?prep=CV1P0341

The Volatile Chemist - 28-1-2016 at 15:25

Sorry, I probably should've checked OrgSyn.
That preparation of course differs on a few points from what has been described here. The tedious chilling, the steam-heating, etc.

wg48temp9 - 12-12-2019 at 04:46

Quote: Originally posted by DraconicAcid  
Quote: Originally posted by The Volatile Chemist  

Does anyone have a source for:
Quote:
Conc H2SO4 is able to polymerise aceton into 1,3,5-trimethylbenzene (mesitylene).

Of course it seems that other users weren't able to perform this anyways.


I know which book I remember reading it in, but don't have it handy.

But it's here: http://www.orgsyn.org/demo.aspx?prep=CV1P0341


Thats a very OTC route to mesitylene. The yield at 13 to 15% is low but the reactants are cheap. I wounder if there is an other procedure that has a better yield.