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@Zale101 this is for you
I guess you could draw the flat ringed structure
Since i believe this to be an SN2, then it should be a concerted reaction. All happen at the same time.
I have a question |dw:1446943977763:dw|
Am i right on the previous one? :x
polar aprotic solvent*
yep the first one is correct. I'm just wondering though if this could also be an E2 reaction or if we would get some E2 product that kind of stumped me but the answer is SN2. i guess I can see why though.
I remember using kmno4 in the lab, this reaction is interesting because kmno4 is purple and when it reacts with an alkene it goes from purple to colorless. you can see the change as it happens.
I would said yes if the nucleophile had a strong base, high temp, or bulky groups.
that's an excellent approach. they didn't give us a temperature either
I am sorry. I couldn't understand the arrows you drew xD
i'M not sure of this is exactly how the mechanism is but the Mn reacts with the double bond let me check this. you get a di-ol. |dw:1446944614071:dw| for this the temperature you do this reaction at is important if it's cold you get a Di-OL hot I think it's oxidation
sorry disregard what I wrote, You get MnO2 as one of the products, MnO4 isn't regnerated
Okay so this is a cycloaddition
|dw:1446944956597:dw| I didn't understand the arrows here :x
Wait nvm i got it!
I know you get an alcohol in the end but I don't see how you would get MnO2 in basic conditions though. It would probably be good for us to go over this mechanism more.
okay so we know that mnO4 adds syn
i'm trying to figure out the mechanism here
for me it's not enough to say oh we get a di-ol as our product
This is the product.|dw:1446945608450:dw|
Yeah, that and its enantiomer because it's a racemic mixture i guess.
I think that's the other enantiomer because the resulting compound doesn't have a plane of symmetry But you see where i'm coming from right? i'm trying to figure out the mechanism for the second part. but for w.e reason they don't show it. it's probably much more complicated than for orgo-I
@Empty your expertise is needed here, you wouldn't mind explaining this mechanism would you?
The second part of the KMNO4 mechanism when we add NaOH/H2O
I don't know what happens, but I could guess. Another thing worth looking into that is similar is Osmium Tetroxide, it very likely goes through the same mechanism, here's a good starting place to see what I'm talking about. http://www.masterorganicchemistry.com/2011/07/01/reagent-friday-oso4-osmium-tetroxide/ For right now I'm looking into it though and trying to see the most plausible mechanism. Admittedly this is sorta inorganic chemistry territory and Manganese and Osmium both have d-orbitals to worry about, so maybe it's worth looking into those? I'll try suggesting a few mechanisms in a bit and we can try to figure out what ones work best. But hey, at least you can derive on your own the crucial fact that it adds syn, which is awesome.
I wonder if they are still trying to figure out how this mechanism works
my prediction is that this reaction isn't fully understood.
as in terms of the mechanism. You could use NMR spec and IR to figure out the presence of an -OH group
I remember doing a lab like this regarding 4-methylcyclohexanol producing 4-methylcyclohexene
We did an IR spectra and see if our reaction proceeded correctly by seeing no appearance of OH group. But it was the other way around
it was more of an elimination reaction
IR is very useful to detect the presence of certain groups but it doesn't really tell you the type of molecule you have, usually in lab they'll have you do that along with H nMR
We did both actually.
I'm actually still looking into this reaction here with the bicyclo [3.1.1] heptane derivative. My first thought was that it would have an elimination, but I think the reason it doesn't is flipping bromine into an axial position is too hindered. I think the space filling model of cyclohexane kinda shows how crammed the molecule is (while the bond line structure makes it seem quite tiny!) https://s10.lite.msu.edu/res/msu/botonl/b_online/fo16/cyc6sfw.gif imagine putting another methylene bridge into this, and now we can't get bromine to flip up from its axial position to do elimination.
yeah that looks pretty crammed. I was wondering about that too because at one point I was thinking hey maybe that could be an elimination too
Hey do you know of any good online apps that do the 3D molecule s and stuff iike that?
No, but funny you should say that, I am actually working on making one right now for Android. :P
guys we need to do this again
I'd really like to know how fast this first reaction takes... It just seems like it'd have trouble doing even a SN2 reaction. I kinda wonder if it's SN1 with the extra methyl groups better supporting it, although they are kind of far away. I bet it rearranges into bicyclo [2.2.1] heptane pretty easily too with certain reagents, kinda interesting I've never really seen this particular one before. Actually that rearrangement's new molecule is known as Norbornane which is quite a famous and disputed molecule because of its cation's bonding. No one really knows what's going on with it, so kinda cool! https://en.wikipedia.org/wiki/2-Norbornyl_cation
Also I agree!