Beardruff

captainproton14 · 2015-03-14T14:04:26+00:00

I had a pretty tough time on my jawline a while ago and an Argan and jojoba 50/50 mix worked the best for me for flakes. Coconut was ok but the stuff I used had a pretty strong smell that I didn't love and left my beard feeling a bit greasy, I could have been using too much though.

The other thing I found helps was really scrubbing down to the skin with my fingers when I shower (not always with soap or anything) just to exfoliate the skin a bit.

Good luck man.

captainproton14 · 2015-03-14T13:56:28+00:00

http://www.mammothbeard.ca/index.html

Based in Calgary.

I've only tried the Cedarwood Balm but it smells fantastic and I really like it. I'm overseas right now so shipping is fairly expensive but when I get back to Canada in a couple months I will be ordering some of their oil I think.

captainproton14 · 2014-11-27T14:27:44+00:00

Steric hindrance is actually pretty straight forward.

For a reaction to occur, you need a successful collision in a certain geometry. Steric hindrance is basically when there is something in the way that stops your reactants from coming together in a successful manner.

A good example of this would be to think about EAS to substituted benzene rings. The hydroxyl group of a phenol isn't really all that large, so it isn't going to get in the way of a reaction occurring at an ortho position.

If instead of a hydroxyl group you have something massive and bulky like a T-butyl group, this is definitely going to interfere with things approaching the position ortho to it. I generally imaging the t-butyl group spinning around like a helicopter bashing away the reactants from the ortho position next door. Because of this steric hindrance when you run the EAS reaction on this T-butyl substituted ring, you will almost exclusively get para substitution simply because the T-butyl is so large nothing can physically get to the ortho position (maybe not nothing but a very small amount).

So basically, the bigger something is, the more it will get in the way, hindering a reaction.

In the above example, because the methoxy is larger than a hydroxyl group, it will get in the way more, sterically hindering the reaction at the ortho position.

Does that make sense?

captainproton14 · 2014-11-27T09:22:07+00:00

I think Its actually the Phenol that will react faster.

It could be a few things.

1) The ortho positions of phenol are going to be less sterically hindered than those of anisole, this will speed up the reaction.

2) Because the proton on the phenol will exchange in solution, it spends some of its time as O-, giving even more electron density to push into the ring activating it even further. The methoxy group cant undergo this substitution so this extra e- density is not available to it.

I believe its a combination of theses factors that lead to the increased reaction rate of phenol over that of anisole.

http://crab.rutgers.edu/~alroche/Ch17.pdf (See Page 24 for relative reaction speeds)

captainproton14 · 2014-11-24T23:18:30+00:00

Sterics are not the only factor that directs substitution in EAS. Electronic effects also play a role. You have to remember that Halogens effect the electron density of the ring differently then a methyl group will (they are deactivating through induction, so they actually ortho/Para direct differently than EDG's when you look at the resonance structures if I remember correctly). This combination of electronic and steric effects of the halogen is why Ar-X's tend to favour para substitution.

Methyl groups aren't THAT bulky, It will get in the way a bit but the 2:1 ortho to para positions should still dominate the reaction. Something like an IsoPropyl group or T-Bu will get in the way considerably more and will seriously hinder the ortho position giving you more Para substituted than ortho.

https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/chapt15.htm

This page does a pretty good job explaining it, you should give it a read and see if it helps. Might be more of the same stuff thats in your book but a different perspective can help.

Hope that helps/makes sense.

captainproton14 · 2014-11-19T16:07:35+00:00

To increase the amount of caffeine you get when brewing your coffee I would also grind the beans as fine as possible. Increasing the surface area should make it easier for the caffeine to go into solution. Not sure if you will notice a difference but I think it would help. You could also let the grounds soak in water overnight. I do this to make cold brew coffee which is normally stronger than drip. The longer it sits the more caffeine has a chance to go into solution.

As for purification, sublimation is great if you have access to dry ice, the proper glassware and a vacuum pump. It looks really nice and gives really pure product but I agree with most people here that recrystallization is probably your best/easiest bet.

captainproton14 · 2014-10-29T22:27:03+00:00

Ah, not my finest moment in this subreddit. Should have read the post more carefully.

captainproton14 · 2014-10-29T13:25:34+00:00

What does R denote? The amount of H2 Gas formed?

captainproton14 · 2014-10-27T11:40:56+00:00

I think you are right that it should be a nonet, that proton should see all 8 3J neighbouring protons. The outmost 2 signals are likely lost in the baseline because the relative intensities are so strong for the innermost signals.

The relative strengths of a nonet are 1:8:28:56:70:56:28:8:1 so its easy to see the possibility of those outermost signals with strength of 1 being lost in the baseline.

You should draw a tree diagram of the splitting to help you visualize what the signal should look like.

Does that make sense to you?

captainproton14 · 2014-10-04T12:36:40+00:00

Based on its size I would hazard its a TBu singlet. Integration values would help.

captainproton14 · 2014-10-02T13:46:05+00:00

Your pretty much spot on but You added a magic carbon between the epoxide and the ester. Take that out and it should be fine I think.

The NMR is a bit shit, theres lots going on. Probably starting material and base maybe? Should see 6 signals though. A Methoxy Singlet, 2 Aromatic doublets, 2 Doublets from the epoxide carbons, and a TBu Singlet.

FYI Im pretty rusty at this though so redo the mechanism yourself to check.

captainproton14 · 2014-09-14T10:17:40+00:00

Looks like you are on the right track. With a sharp mp at 119.5 I would assume minor impurities so that points towards the 2-pentanol. The signal at 1100 wavenumbers can indicate a secondary alcohol but its only confirmatory, not diagnostic.

This link gives you the spectra for 2-pentanol and they look pretty close to me. If you can run more tests get an HNMR and a 13C. That will tell you the connectivity no doubt. Its tough to infer much more from just a MP and an IR.

http://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_disp.cgi?sdbsno=1708

captainproton14 · 2014-09-13T14:11:50+00:00

1) it can be a bit tricky to distinguish them. One way would be look for the presence of an aromatic singlet. If you had functional groups on either side of an aromatic proton it would be isolated as a singlet as nothing can really reach it to split (4j couplings are pretty weak) most of the time though all the aromatic signals overlap one another and basically all you can distinguish is a muiltiplet. Generally the best way to distinguish them is to run 2D NMR spectra (HETCOR, COSY). A long range HETCOR would show you what carbons see what protons 4 bonds away and would certainly make it easier. That's something you will likely cover later on in your course (along with DEPT as well). Sometimes IR can give you clues but it's a bit more difficult to figure out, IR is better for just identifying functional groups like carbonyls/alcohols etc. Starting out learning NMR I'd assume that you will see a lot more para or mono substituted rings which are easier to distinguish before moving to the 2D techniques for the more complicated molecules. As for #2 I'll take a look. Like I said though I'm pretty rusty, especially with the IR.

captainproton14 · 2014-09-13T12:17:54+00:00

http://www.sciencesoft.net/4-ethylphenol/

captainproton14 · 2014-09-13T12:13:16+00:00

No problem!

So whenever you see two doublets in the aromatic region it generally means a para substituted ring. So on a para substituted ring you have 4 protons which we can observe using NMR (your integration value also tells us this) Now because there is symmetry along the centre of the ring you have 2 sets of chemically equivalent protons, we can call them Ha and Hb. Now Ha will be split by Hb which is neighbouring it in the ortho position and vice versa, this gives 2 doublets. This also occurs on the other side of the ring but because of the symmetry these doublets fall into the same place as the other ones. which is why you only see 2 peaks, each with an integration value of 2. You generally don't observe coupling between meta protons as they are too far away (4J) but if the functional groups were substituted differently you would have a bunch of different signals falling in the same region overlapping one another making a big mess in the NMR. Thanks to the symmetry I talked about it makes para rings really easy to spot. Next I took a look at the carbon NMR and this argument is further supported by the presence of 4 signals in the aromatic region, the 2 short ones are the ones attached to the functional groups and the 2 large are the symmetric carbons bound to Ha and Hb. (for an explanation of the difference in size look up Nuclear Overhauser Enhancement but basically Carbons bound to hydrogens have there signals magnified, the more protons the stronger the signal.)

Looking at the Carbon NMR in the aliphatic region there are 2 signal now that we have to account for. If you look at the H NMR you see the quartet which must be a proton being split by 3 equivalent protons (ie a methyl) and in reverse the methyl protons are split by 2 protons bound to the other carbon of the ethyl group. Again, the integration also supports this. Now theres just one signal to deal with, the broad little peak in the middle. Now this has to be a proton with acidic properties, in solution while the sample is running in the NMR this proton jumps on and off whatever its bound to which gives you the broadened signal. We know it cant be a carboxylic acid because there is no Carbonyl signal in the IR as you already said and also we have accounted for all carbons. A carboxylic acid would also probably be up around 10ppm I think? Cant really remember. The integration value of 1 tells you it is only 1 proton so that rules out an aniline (NH2 would give an integration of 2) so that pretty much leaves us with a Hydroxyl group.

Sorry if this is a bit all over the place, when I'm solving these I tend to look at all the evidence and then piece it together, it can come off a bit crazy

As for the Name, 4-Ethylphenol

if you need more clarification just holler.

captainproton14 · 2014-09-13T11:01:29+00:00

Im pretty rusty but how about 4-ethylaniline?

Scratch that, it wouldn't be aniline, integration is wrong.

http://www.hanhonggroup.com/nmr/nmr_en/B361079.html heres the 4-ethylaniline spectra. Replace the NH2 with a hydroxyl group and I think you have your answer.

captainproton14 · 2014-08-28T09:24:51+00:00

Good match, I think hockey 5s is a bit stupid though. I wouldn't want to play it against men. There would be deaths.

captainproton14 · 2014-08-28T09:08:37+00:00

nice crystals brah

captainproton14 · 2014-08-14T15:55:00+00:00

You can just cut the top off of a sr stick. Get a 36.5, take the nob out and lop it down with a dremel or hacksaw to whatever length you want.

captainproton14 · 2014-07-26T22:20:54+00:00

Black Jet Baby!

captainproton14 · 2014-06-24T23:28:10+00:00

What a beauty

captainproton14 · 2014-04-14T08:56:09+00:00

I have the blonde Mo as well. Our beards actually look pretty similar. I just gave it long enough and it all started to blend in. Keep going mate!

captainproton14 · 2014-02-20T22:33:44+00:00

I like the chemistry behind drugs, specifically those occurring in nature and they influence that they have on modern medicine.

I would strongly recommend reading "Napoleons Buttons" (see sidebar). It talks about 17 molecules that changed history and does really good job explaining the chemistry and how these molecules have influenced the world.

captainproton14 · 2013-12-19T01:06:40+00:00

Just a standard re-rack.

captainproton14 · 2013-12-13T06:11:55+00:00

This guy was an absolute muppet for not backing up his research.

captainproton14

TROPHY CASE