ngeneerguy - 26-3-2007 at 07:47
finally got a topic of interest!! trying to do a reduction with chlorox using a conjugated diene with an alcohol group attached, reducing to a
keytone. the intel on it tells me that i should be working with an endo but all i have to work with is an exo. will this affect on the reaction???
and, in truth, does this reaction realy work?
[Edited on 27-3-2007 by chemoleo]
Sauron - 26-3-2007 at 07:55
Reducing an alcohol to a ketone?
No, you are oxidizing an alcohol ( secondary one) to a ketone.
If you were transforming a ketone into an alcohol that would be a reduction, of course you would not be using hypochlorite to do that would you?
I'll let someone else speak to the exo/endo issue, hopefully someone who knows about this!
BTW don't you think this thread deserves a more topical name than my handle? Otherwise it will only serve to make the search engine less useful than
it already is. The thread is not about me, or even about Tolkein demons.
[Edited on 26-3-2007 by Sauron]
Nicodem - 26-3-2007 at 09:09
WTF? A thread called "sauron" containing some incomprehensible blather?
This is getting extremely pathological.
Pyridinium - 26-3-2007 at 09:18
If you're talking about exo / endo attack based on steric hindrance, can you provide a name for the conjugated diene, or perhaps a diagram? Where is
the -OH group attached?
This might help.
Ah, Sauron, you're developing a cult of personality. All you need now is your own Black Tower.
Sauron - 26-3-2007 at 09:21
Already under construction.
As to the cult of personality, if nominated I will not accept. If elected I will not serve.
ngeneerguy - 26-3-2007 at 14:23
sorry bout the thread name sauron...didnt really know how to send ya a private msg with this board. and yes i know that im not reducing...just got in
a hurry and was pressed to get a msg out between classes. the endo product im supposed to be workin with is just a 6 carbon base ring with a 1 carbon
bridge and the OH group is on the carbon just next to the bridge. the exo product is almost the same except for the placement of the OH group. i
couldnt find anything that was majorly significant about the difference but wanted to see if anyone might know if there was a reason this might not
work the same.
as for the thread...i will refrain from using your name to start a thread again and if i do it will be about "Tolkein demons" or some such subject
matter.
chemoleo - 26-3-2007 at 16:57
I was just about to change the thread title, but then I realised I didn't understand what the thread is about! Chlorox-based *reduction* of diene
alcohols to ketones? 
?
Levi - 26-3-2007 at 17:01
It is possible to use oxidizers as reducing agents. I once knew a guy who used a large amount of NH<sub>4</sub>NO<sub>3</sub>
to reduce some organic matter to a smoldering hole in the ground. 
[Edited on 26-3-2007 by Levi]
Sauron - 26-3-2007 at 18:09
That's using "reduce" in the military sense.
Here's your ketone. I have drawn in the pi bonds because you didn't specify where they are, only that they are conjugated. I can see at least two
different such arrangements. So here are both.
The ketone looks fat and happt (stable.) However as soon as it is oxidized, I bet that -OH group will really want to eliminate and form a third pi
bond which will be conjugated to both of the others (in both possible arrangements of where your first two double bonds are.) Best do this oxidation
in the cold to have much chance of isolating the alcohol, I suspect.
[Edited on 27-3-2007 by Sauron]
ngeneerguy - 27-3-2007 at 01:51
in all the literature that ive read about this reaction says that it should be done where the temp doesnt exceed 20 deg C and some slightly less. the
second image is the product that im expecting out of the reaction. another thing i have read is that, if not properly observed, this reaction can
become very exothermic. the reason ive asked about it is because my prof has said that even though he has seen people attempt it, he has never seen
anyone successful in doing anything but making a smelly, goopy mess of the original reactant and chlorox. didnt want to start this and end up with
much the same thing but i guess it is a matter of paying close attention as with any other reaction, which seems to be a running thing with some
students and their labwork. put a kid in front of a perfectly good chem set and watch em screw something up every time
Sauron - 27-3-2007 at 02:18
Let us have the literature on this and we will see if we can figure out what is going wrong (when others attempted it) and how to do it succesfully.
Maybe a different oxidizing agent?