NileRed - 2014-06-09
In this video, I will be making n-bromopropane by brominating 1-propanol. The n-bromopropane can then be used in a Grignard reaction to make butyric acid (smell of vomit). Here is the video of me using it in a Grignard reaction: http://youtu.be/_wmx65zQk58 This process can be used as a general procedure to produce bromoalkane. For example, it can be used to make n-bromobutane, which can then be used to make n-Butyl Lithium.
yessss thank you
Hey, love your videos! You mention the Grignard reaction. Can you possibly make a Wittig Reaction video? it's a great reaction and I'd love to see it in action!
Thanks!
Edexcel Chemistry IAL Unit 3 (Alternative to practical) paper: 2015 Q4 !!! XD
hello, live your videos, i think I've watched and liked every one of them! i have a question for NileRed if you don't mind, you as a chemist know that bromine is toxic. so how is brominated vegitable oil not toxic... that product is in most fruit or citrus soda pop, among many other edible products. thanks for your time, hope you can reply.
Hey, I’m a Junior currently attaining a chemical engineering degree. Your concern is a somewhat reasonable one, as patients have presented with conditions like bromoderma from excess intake of brominated vegetable oils. One particular case was a man who was drinking 8 liters of Ruby Red Squirt every day, however. Other cases also indicate that large amounts of the oil are necessary to cause any effects. The FDA labels it as generally recognized as safe because of this, but the EU has banned it. Anything is toxic in large enough quantities, so both decisions regarding its safety are fairly reasonable. Bromine can be removed from blood via dialysis in extreme cases, something that renders bromine ailments from the oil even less concerning than their rarity already does.
You can also leave soon after the synthesis of bromo acetone?
Every time you work with something dangerous like a carcinogen or whatever I worry abt ur health. Stay safe!!
I sell bromopropane, and bromopropane accessories
Can you do a synthesis for acetic anhydride please and thank you ?!
I plan to try it eventually. The synthesis routes are kind of dangerous to do at home though.
I would prefer to work via private messages. Feel free to send me one!
I did. please get back to me
Another great video! Im glad that you are doing more organic chemistry, i think that it is far more interesting.
Quick question: Can the same procedure be applied to alkenes? Theoretically it works out nicely with Markovnikov's Rule, but i think there might be a side hydration reaction that would ruin the yield. Any ideas?
From what I've read from this link, it seems more than possible.
http://www.chem.ucalgary.ca/courses/350/Carey5th/Ch06/ch6-4-2.html
could any one tell me how moisture sensitive alkyl halogens are ? is it necessary to handle them under inert gas ?
Can this be applied with other acids, such as hydrochloric?
@DFliyerz yes, but bromine is a significantly better leaving group compared to chlorine, so a chlorinated alkane is not nearly as good of a grignard reagent as a brominated alkane.
Can this be done with any other acid than sulphuric acid?
For various reasons sulphuric acid is heavily regulated here.
Could I produce bromoethane this way? I want to try making diethyl ether viz Williamson ether synthesis and so I need an ethylhalide
I am not totally sure. An excess for sure. You can calculate the concentration and amount that the in situ method makes and just use that.
After calculating the mols of Br in the salt, and the mols used, I found 0.193 was the answer. Then using molar masses I got that 0.194 mols of Br in HBr would be the same, and eventually got an answer of about 16 grams of HBr gas would be needed. Using azeotropic HBr being 47.6%, I calculated i would need around 33 grams of that, or about 26 mL based on density. Am I close?
Even though I ended up just going with solid NaBr instead because my HBr didn't seem very good. Been trying to fractionally distill it but it's been going all day and still boils at under 80C so I'm starting to think my acid is bad :l
The product you got boiled around 80C? Also, if distilling out of the reaction vessel, i would just do a simple distillation. Remove the water and then distill it (fractionally maybe) again if you like.
I don't think your sulfuric acid can really go bad!
I tested the distillate on aluminum and nothing happened, so I don't think any HBr came over.
Please bromoacetone synthesis of glacial acetic acid and acetone and bromine into your channel
Could KBr be used instead of NaBr?
Mack3nzie Dravid yep
Yes, if course.
Yes. The sulfuric acid is used to swap the alkali metal to a hydrogen so bromide ions will be present to react with the alcohol. The only difference between NaBr and KBr will be the formation of either NaHSO4 versus KHSO4. (NaBr is preferable purely due to availability, rather than chemical reactivity.)
Mack3nzie Dravid yes, KBr will definitely work. However, you will have to use more of it, because KBr’s molar mass is greater than that of NaBr, because potassium is heavier than sodium. In other words, you will have to use more KBr (with the same amount of H2SO4 used in this video) to attain the desired stoichiometry.
Of corpse
how do you make 1 propanol from 2 propanol
you should make a video on this. thanks :)
@Nile Red cant you just make it from the butane in lighters.
@science Vlog Lighters have regular butane in them which is just single carbon chain. Adding an alcohol to this will have little to no specificity. Also, working with a gas reagent is kind of a pain.
true, the butanol was to make tributyl phosphate but ill just make trimethyl
phosphate
@science Vlog It's a lot easier just to buy butanol off amazon (or tert-butanol, they have that too)
can 2-propanol be used? or even better, could the Grignard reagent be constructed from n-hexane?
@AddisonPhilips The bromination of n-hexane requires elemental bromine and high temperatures, as for 2-propanol--that should work, except you will produce
2-bromopropane
There's a much better use for the 1-bromopropane grignard than making the smell of vomit. It can react with acetone to form 2M2B, a.k.a. the 4000 proof alcohol.
+avrorik369 really
could you use HBr instead of H2SO4/NaBr mixture?
gustavo espinoza hey says it in the video... just pay attention.
Wwhhhooaa there, you mixed water with an akyl halide, wouldn't that be kinda counter productive, like wouldn't there be an Sn2 reaction between the akyl halide and the water to give you back your alcohol???!?!
marialiyubman - 2020-01-08
Is this reaction toxic?
NaBro.
My teachers are you and chemistry cat.