Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Oxidation of salicylic acid to 1,2 benzoic acid
Jmap science
Yet another ID of SimpleChemist-238
*




Posts: 40
Registered: 19-10-2013
Location: Florida
Member Is Offline

Mood: No Mood

[*] posted on 6-11-2013 at 09:54
Oxidation of salicylic acid to 1,2 benzoic acid


Because salicylic acid acts as a alcohol is it possible to use KMnO4 to further oxidize the hydroxyl group to a carboxylic acid, yielding MnO2 and Potassium 1,2 benzoic acid. Im just a beginner in organic chemistry. :D
View user's profile Visit user's homepage View All Posts By User
DraconicAcid
International Hazard
*****




Posts: 4278
Registered: 1-2-2013
Location: The tiniest college campus ever....
Member Is Offline

Mood: Semi-victorious.

[*] posted on 6-11-2013 at 09:59


Where would the extra carbon come from? Salicylic acid is a phenol- an oxidizing agent such as KMnO4 is not going to do the conversion ROH -> RCO2H.



Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
View user's profile View All Posts By User
Lambda-Eyde
National Hazard
****




Posts: 857
Registered: 20-11-2008
Location: Norway
Member Is Offline

Mood: Cleaved

[*] posted on 6-11-2013 at 09:59


No. If you study the structures of the two side by side (and understand what the structural formulae tell you) you should be able to figure out why. Also, such topics belong in the "Beginnings" section.



This just in: 95,5 % of the world population lives outside the USA
You should really listen to ABBA
Please drop by our IRC channel: #sciencemadness @ irc.efnet.org
View user's profile View All Posts By User
Nicodem
Super Moderator
Thread Moved
6-11-2013 at 10:47
Hexavalent
International Hazard
*****




Posts: 1564
Registered: 29-12-2011
Location: Wales, UK
Member Is Offline

Mood: Pericyclic

[*] posted on 6-11-2013 at 14:57


I'm feeling quite patient this evening, so I've made a quick reaction scheme for what you are proposing, showing all of the carbon atoms in addition to the standard functional groups and terminal carbons. As you can see in red and as DraconicAcid pointed out, a carbon magically appears in your product, which is impossible.


salicyl oxidation.gif - 2kB

[Edited on 6-11-2013 by Hexavalent]




"Success is going from failure to failure without loss of enthusiasm." Winston Churchill
View user's profile View All Posts By User
deltaH
Dangerous source of unreferenced speculation
*****




Posts: 1663
Registered: 30-9-2013
Location: South Africa
Member Is Offline

Mood: Heavily protonated

[*] posted on 6-11-2013 at 23:32


In 2053 the nobel prize for chemistry shall have been awarded (sorry tenses get very complicated with time travel) for the development of a homogeneous catalyst that inserts CO resulting in the conversion of a phenolic group to an aromatic carboxylic acid.

In his acceptance speech, said winner will have gone on to state that inspiration for this came from a science forum some forty years prior ;)

EDIT:

Huh... I've just checked the rule book and apparently while I am not permitted to give the details of this, I am permitted of giving abstract clues about it... so here goes:

pic1.jpg - 6kB pic2.jpg - 13kBpic3.jpg - 6kB pic4.jpg - 4kB

[Edited on 7-11-2013 by deltaH]




Mind your step or step your mind. Website: www.ideashack.org
View user's profile Visit user's homepage View All Posts By User
bfesser
Resident Wikipedian
*****




Posts: 2114
Registered: 29-1-2008
Member Is Offline

Mood: No Mood

[*] posted on 7-11-2013 at 09:37


Alright, the OP's question has been answered, and this thread is now obsolete. [closed]

<img src="../scipics/_warn.png" /> deltaH, save the spam for Whimsy. <img src="../scipics/_warn.png" />




View user's profile View All Posts By User

  Go To Top