Sciencemadness Discussion Board

Hex- Prefix

thebean - 1-3-2014 at 12:16

I've become increasingly interested in hex- prefix containing compounds. I think it's because I like the sound of it :D. 2-Ethylhexanol is a pretty simple one from gloves. But I want something that can easily donate the hex- prefix into other compounds. I'm hoping to produce hexanoic acid at least. I took a look at the longer chain tertiary alcohols thread in organic chemistry but I couldn't seem to find a whole lot.

thesmug - 1-3-2014 at 13:18

Quote: Originally posted by thebean  
I've become increasingly interested in hex- prefix containing compounds. I think it's because I like the sound of it :D. 2-Ethylhexanol is a pretty simple one from gloves. But I want something that can easily donate the hex- prefix into other compounds. I'm hoping to produce hexanoic acid at least. I took a look at the longer chain tertiary alcohols thread in organic chemistry but I couldn't seem to find a whole lot.

I think that hexane or cyclohexane would be your best choice. I'm no expert but I think benzene might also.
[EDIT] I looked up that 2-Ethylhexanol and it is just hexane with some other groups added, so yeah, hexane or cyclohexane.

[Edited on 3/1/14 by thesmug]

thebean - 1-3-2014 at 13:42

I figured as much but would mixed isomers of hexane work?

ScienceHideout - 1-3-2014 at 17:50

Look into the Grignard reaction... you can use that to make a lot of interesting compounds with hex chains...

If I am not mistaken, can't hexanol be made of pentanol and and formaldehyde?

[Edited on 2-3-2014 by ScienceHideout]

Brain&Force - 1-3-2014 at 18:47

What about the awesomely triboluminescent hexakis(antipyrine)terbium iodide? Difficult to acquire and make but definitely worth it.

And don't forget your hexaammine complexes of nickel, cobalt, and others.

thesmug - 1-3-2014 at 19:14

Quote: Originally posted by Brain&Force  
And don't forget your hexaammine complexes of nickel, cobalt, and others.

I've made hexaaminenickel(II) chloride and I have to say it was the easiest and possibly most fun reaction I've ever done. For some reason filtering out the precipitate from this reaction is so much easier than any other! I highly recommend you (OP) try it.

Hexavalent - 2-3-2014 at 13:48

Quote: Originally posted by thebean  
But I want something that can easily donate the hex- prefix into other compounds.


Do you have an understanding of simple organic chemistry?

Are you telling us that you want to prepare a series of compounds including six carbons as the parent chain, is this your intention? Or are you interested in simply preparing any compound which has a "hex-" prefix in its name?

If the former, and you're not concerned about the 2-ethyl substitution, then it will undergo typical primary alcohol reactions; you can produce the carboxylic acid, 2-ethylhexanoic acid, by oxidation with acidified dichromate. More carefully-controlled oxidation could afford the aldehyde, 2-ethylhexanal.

If you were to begin with hexane, you could attempt a halogenation, although a mixture of isomers would be produced which may be difficult to separate. Given your apparent lack of experience, I would avoid these, but theoretically you may be able to perform an alkylation to deliver the equivalent of the hexyl cation/anion (depends if your alkylating agent is electrophillic or nucleophillic) onto your substrate of choice, if possible. I would expect a Friedel-Crafts alkylation or similar to be possible.

If the latter, then a greater depth of field is naturally possible: co-ordination chemistry springs to mind, with the aforementioned complexes which are relatively easy to prepare and are rewarding for the beginning chemist.

@ScienceHideout - I can't imagine a direct reaction like that, but I recall reading that halogenation of the lower alcohol, followed by treatment with a Grignard reagent, then reaction with formaldehyde then protonation, affords the higher alcohol.

[Edited on 2-3-2014 by Hexavalent]

thesmug - 2-3-2014 at 15:49

Quote: Originally posted by Hexavalent  
Quote: Originally posted by thebean  
But I want something that can easily donate the hex- prefix into other compounds.


Do you have an understanding of simple organic chemistry?

Are you telling us that you want to prepare a series of compounds including six carbons as the parent chain, is this your intention? Or are you interested in simply preparing any compound which has a "hex-" prefix in its name?

If the former, and you're not concerned about the 2-ethyl substitution, then it will undergo typical primary alcohol reactions; you can produce the carboxylic acid, 2-ethylhexanoic acid, by oxidation with acidified dichromate. More carefully-controlled oxidation could afford the aldehyde, 2-ethylhexanal.

If you were to begin with hexane, you could attempt a halogenation, although a mixture of isomers would be produced which may be difficult to separate. Given your apparent lack of experience, I would avoid these, but theoretically you may be able to perform an alkylation to deliver the equivalent of the hexyl cation/anion (depends if your alkylating agent is electrophillic or nucleophillic) onto your substrate of choice, if possible. I would expect a Friedel-Crafts alkylation or similar to be possible.

If the latter, then a greater depth of field is naturally possible: co-ordination chemistry springs to mind, with the aforementioned complexes which are relatively easy to prepare and are rewarding for the beginning chemist.

@ScienceHideout - I can't imagine a direct reaction like that, but I recall reading that halogenation of the lower alcohol, followed by treatment with a Grignard reagent, then reaction with formaldehyde then protonation, affords the higher alcohol.

[Edited on 2-3-2014 by Hexavalent]

Your username is very relevant :P

thebean - 2-3-2014 at 18:40

Quote: Originally posted by Hexavalent  
Quote: Originally posted by thebean  
But I want something that can easily donate the hex- prefix into other compounds.


Do you have an understanding of simple organic chemistry?

Are you telling us that you want to prepare a series of compounds including six carbons as the parent chain, is this your intention? Or are you interested in simply preparing any compound which has a "hex-" prefix in its name?

If the former, and you're not concerned about the 2-ethyl substitution, then it will undergo typical primary alcohol reactions; you can produce the carboxylic acid, 2-ethylhexanoic acid, by oxidation with acidified dichromate. More carefully-controlled oxidation could afford the aldehyde, 2-ethylhexanal.

If you were to begin with hexane, you could attempt a halogenation, although a mixture of isomers would be produced which may be difficult to separate. Given your apparent lack of experience, I would avoid these, but theoretically you may be able to perform an alkylation to deliver the equivalent of the hexyl cation/anion (depends if your alkylating agent is electrophillic or nucleophillic) onto your substrate of choice, if possible. I would expect a Friedel-Crafts alkylation or similar to be possible.

If the latter, then a greater depth of field is naturally possible: co-ordination chemistry springs to mind, with the aforementioned complexes which are relatively easy to prepare and are rewarding for the beginning chemist.

@ScienceHideout - I can't imagine a direct reaction like that, but I recall reading that halogenation of the lower alcohol, followed by treatment with a Grignard reagent, then reaction with formaldehyde then protonation, affords the higher alcohol.

[Edited on 2-3-2014 by Hexavalent]


I'm aware that my question was rather vague, that's why I posted to beginnings. I was interested in having a six carbon chain. My knowledge of organic chemistry is pretty decent. I was considering halogenation of hexanes but I don't have anything that would make separating the isomers very easy. I would appreciate it if you didn't patronize me.

[Edited on 3-3-2014 by thebean]

Töilet Plünger - 2-3-2014 at 19:11

What about hexahalobenzene compounds?
Or hexamethylbenzene?
Or hexyl compounds, such as hexyl acetate, hexyl benzoate, or dihexylmercury?

thebean - 2-3-2014 at 19:30

I'll pass on the dihexylmercury :P but everything else sounds good.

DraconicAcid - 2-3-2014 at 19:42

Tungsten hexachloride?

Pyrovus - 3-3-2014 at 02:10

Hexahexyl hexhexhexium? Might be difficult to make, though.

Mesa - 3-3-2014 at 06:42

Quote: Originally posted by DraconicAcid  
Tungsten hexachloride?


This compound is frustratingly difficult to prepare, any oxygen present during the reaction results in a self sustaining oxidation of the tungsten and a mix of oxide and oxychlorides:mad:.

@OP:
The issue is that simply wanting to prepare anything with a hex prefix/suffix gives far too wide a scope for useful suggestions.

I looked up a list of isomers of decane and counted 23 individual isomers containing 'hex.' That's just C10 alkanes. every other functional group also has the possibility of forming isomers with a CH3-CH2-CH2-CH2-CH2-CH2 chain(given it has >6 carbon atoms.)

Then on to inorganic...

DraconicAcid - 3-3-2014 at 10:23

I'm sure you don't want to try making chromium hexacarbonyl or potassium hexacyanoferrate.

ETA: Well, I'm guessing you probably don't want to make potassium hexacyanoferrate using cyanide, at least, since I get nervous around cyanides. But I do seem to recall that there is a way to make it without using cyanides....

[Edited on 3-3-2014 by DraconicAcid]

blogfast25 - 3-3-2014 at 12:28

Hexyl hexyl ketone?

warteo - 3-3-2014 at 16:02

As others have mentioned, some of the Hexaammine coordination compounds suit your request.

Going to give making these a try when I get hold of some Ammonium acetate:
Hexaamminecobalt(III) acetate and chloride
Synthesis of Hexamminecobalt(III) Chloride

Once the Hexaamminecobalt(III) chloride is prepared it could be fun to take things further and use it to make Hexaamminecobalt(III) pentachlorocuprate(II) or even better for your search, Hexaamminecobalt(III) hexachloroferrate(III).

Some more interesting HEX- compounds are described in here that I'm also planning on trying:
TRANSITION METAL p-TOLUENESULFONATES

DraconicAcid - 3-3-2014 at 16:06

Quote: Originally posted by warteo  

Once the Hexaamminecobalt(III) chloride is prepared it could be fun to take things further and use it to make Hexaamminecobalt(III) pentachlorocuprate(II) or even better for your search, Hexaamminecobalt(III) hexachloroferrate(III).


I would expect the tetrachloroferrate(III) to be more stable. Do you have a cite for the hexachloroferrate?

warteo - 3-3-2014 at 16:18

Quote: Originally posted by DraconicAcid  
Quote: Originally posted by warteo  

Once the Hexaamminecobalt(III) chloride is prepared it could be fun to take things further and use it to make Hexaamminecobalt(III) pentachlorocuprate(II) or even better for your search, Hexaamminecobalt(III) hexachloroferrate(III).


I would expect the tetrachloroferrate(III) to be more stable. Do you have a cite for the hexachloroferrate?


Sure, saw it on P.48, Vol. 11 of Inorganic Synthesis. More interested in making the pentachlorocuprate myself but included this for the double hex factor.

DraconicAcid - 3-3-2014 at 16:21

Quote: Originally posted by warteo  
Quote: Originally posted by DraconicAcid  
Quote: Originally posted by warteo  

Once the Hexaamminecobalt(III) chloride is prepared it could be fun to take things further and use it to make Hexaamminecobalt(III) pentachlorocuprate(II) or even better for your search, Hexaamminecobalt(III) hexachloroferrate(III).


I would expect the tetrachloroferrate(III) to be more stable. Do you have a cite for the hexachloroferrate?


Sure, saw it on P.48, Vol. 11 of Inorganic Synthesis. More interested in making the pentachlorocuprate myself but included this for the double hex factor.


OK- google books wasn't willing to show me that page. I suppose the hexamminecobalt(III) ion is large enough to stabilize the hexachloroferrate(III) ion....

warteo - 3-3-2014 at 16:42

Quote: Originally posted by DraconicAcid  
Quote: Originally posted by warteo  
Quote: Originally posted by DraconicAcid  
Quote: Originally posted by warteo  

Once the Hexaamminecobalt(III) chloride is prepared it could be fun to take things further and use it to make Hexaamminecobalt(III) pentachlorocuprate(II) or even better for your search, Hexaamminecobalt(III) hexachloroferrate(III).


I would expect the tetrachloroferrate(III) to be more stable. Do you have a cite for the hexachloroferrate?


Sure, saw it on P.48, Vol. 11 of Inorganic Synthesis. More interested in making the pentachlorocuprate myself but included this for the double hex factor.


OK- google books wasn't willing to show me that page. I suppose the hexamminecobalt(III) ion is large enough to stabilize the hexachloroferrate(III) ion....


Sorry, I should have provided a link. I sometimes forget that what I have saved locally is not visible to everyone. Here you go -
Inorganic Synthesis, Vol 11 on archive.org

Brain&Force - 3-3-2014 at 17:20

The hexafluorochromate complex appears to exist, that would be interesting.
http://www.chemspider.com/Chemical-Structure.4574204.html

Hexaamminechromium(III) pentachlorocuprate also exists:
http://pubs.acs.org/doi/abs/10.1021/ic50064a012

DraconicAcid - 3-3-2014 at 20:15

Potassium hexafluoroferrate(III) and hexafluoroaluminate exist.

blogfast25 - 4-3-2014 at 05:35

Hexachlorostannate, hexachloroantimonate. Both quite easy.

thebean - 4-3-2014 at 09:15

I should have done a better job explaining that I'm interested in six carbon chains but while looking through this I liked some of the suggestions that were inorganic. Once I get some nitrogen cylinders I'm going to give the tungsten hexachloride synthesis a go. The hexamine complexes sound interesting. Out of curiosity are the hexamine complexes energetic in any cases?

DraconicAcid - 4-3-2014 at 09:23

Quote: Originally posted by thebean  
I should have done a better job explaining that I'm interested in six carbon chains but while looking through this I liked some of the suggestions that were inorganic. Once I get some nitrogen cylinders I'm going to give the tungsten hexachloride synthesis a go. The hexamine complexes sound interesting. Out of curiosity are the hexamine complexes energetic in any cases?


Only if there are lots of nitrate or perchlorate counterions.

Hexavalent - 4-3-2014 at 10:36

Quote: Originally posted by thebean  

I'm aware that my question was rather vague, that's why I posted to beginnings. I was interested in having a six carbon chain. My knowledge of organic chemistry is pretty decent. I was considering halogenation of hexanes but I don't have anything that would make separating the isomers very easy. I would appreciate it if you didn't patronize me.


If you knew your question was vague, and you knew that you wanted a six-membered chain, then why not clarify so in your original question? I have to question your understanding of organic chemistry and general abilities as a scientist if you are unable to deduce such simple matters.

I suspect that most people would have difficulty separating the various isomers of the hexyl halides; perhaps, instead of looking at it directly, an interesting idea for you would be to consider further substitutions and chemical reactions to the substrates to aid in separation. I would be very interested to see such results.

Besides, what do you make of my other suggestions? Although Cr6+ reagents are toxic and likely carcinogenic, the conversion of the primary alcohol to the analogous carboxylic acid should be facile. Conversion to the aldehyde would require more skill and control over the reaction, but is nonetheless a rewarding experience. If you don't want to use Cr6+, then other oxidants are almost certainly possible.

forgottenpassword - 4-3-2014 at 11:20

Will you be doing these experiments with 6 testubes, 6 pipettes, 6 isomers, 6 salts and a labcoat with 6666666666 written all over it?

thebean - 4-3-2014 at 11:53

Hexavalent, I liked the dichromate carboxylic acid synthesis and was planning on carrying it out soon.

Hexavalent - 4-3-2014 at 12:03

Quote: Originally posted by thebean  
Hexavalent, I liked the dichromate carboxylic acid synthesis and was planning on carrying it out soon.


Good! Don't forget to use acidified dichromate; many procedures are available online as this is a common A-level experiment. The colour transition from orange Cr6+ to green Cr3+ is also interesting to observe.

If you need any help with the procedure at all, send me a U2U and I'd be happy to help. :)

DraconicAcid - 4-3-2014 at 13:10

You can make hexanedioic acid (adipic acid) by reacting cyclohexanol or cyclohexanone with hot nitric acid. You need a fume hood for this reaction (huge clouds of NO2 being given off), and have to be careful to avoid a volcano-like eruption, but it is a fun reaction to do.