> chemistry > composés-halogénés > make-alkyl-halides-bromoethane-and-bromohexane-nurdrage

Make Alkyl Halides Bromoethane and Bromohexane

NurdRage - 2017-11-04

In this video we make the alkyl halides bromoethane and bromohexane by nucleophilic substitution of alcohol under acidic conditions.

the highest yielding method is to use alcohol with hydrobromic acid and sulfuric acid. To make bromoethane 350g of 48% hydrobromic acid, 120mL of ethanol and 145mL of sulfuric acid were combined in a flask cooled in ice with plenty of time between additions to allow full cooling. The mixture was then gently heated to 40 degrees Celsius and slowly ramped to 70 Celsius to distill off the bromoethane that forms. What's happening is the classic Sn2 nucleophilic substitution reaction taught in basic organic chemistry. The alcohol is protonated by the acid conditions and essentially forms water still attached to the carbon backbone. Bromide ions come in and attack the carbon and the water leaves. This forms bromoethane. The bromohexane is washed with water and 5% sodium bicarbonate solutions before being dried with anhydrous magnesium sulfate.

Bromohexane is made in a similar fashion. 1 mole of 1-hexanol is mixed with 1.5 moles of sodium bromide and 2 moles of sulfuric acid. the mixture is refluxed for six hours and the bromohexane is recovered using a separatory funnel. it is then distilled and washed. Then fractionally distilled to remove water. 

Related videos:
Make hydrobromic acid: https://www.youtube.com/watch?v=C3n4Xqfb9qk

Make Chloroform: https://www.youtube.com/watch?v=MvkuqLxQd2c

Make chlororobenzyl chloride: https://www.youtube.com/watch?v=4DQuv6LjB80

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Dalitas D - 2017-11-04

you have no idea how much it rubs me the wrong way to see the receiving flask on the left hand side of the destillation flask

Maggie P - 2018-12-05


Ben Earhart - 2019-08-13

I roll left side. It's an elite technique.

Gregory Lazzarino - 2020-03-29

Dude for real.

Andrew Villalobos - 2020-07-23

@Yata Garasu He has a clamp at the liebig condenser and another at the joint between the distillation flask and adapter.

Leandro Paiva Abboud - 2021-02-02

what's the problem?

Jason Patowsky - 2017-11-04

"Hi, that's corrosive, this is flammable, sniff that and you'll get cancer. Ok let's get started!"

This is why I love this channel

Entenkommando - 2017-11-05

I would love him to say that in the into :D

TheHector - 2017-11-05

today we will be making sodium chloride. Before we begin, i must crush your expectations: this isnt cheaper than buying NaCl. we are doing this to explore the science

NetRolller3D - 2019-02-15

Warning: Dihydrogen monoxide is a known asphyxiant.

Bon Bon - 2021-01-08

Yeah, I was always wondering why such disclaimers at all if we're doing it anyway :q It would make much more sense if that disclaimer were followed by a short instruction about HOW EXACTLY we should do it to NOT get cancer, and for contrast, what could go wrong instead to give us cancer :q (so that we knew what to avoid).

Bon Bon - 2021-01-08

@TheHector And yet we still won't gonna eat it, right? :q

NurdRage - 2017-11-04

One my grignards failed disastrously so that video will be delayed, hopefully it'll be out before the end of the year. Next video should be an update on my hotplates that i repaired last year.

highlander723 - 2017-11-04

NurdRage Added the Bromine Compound too fast huh... ya that happened to me once. Got so hot it flashed boiled and the pressure blew the top of the reflux condenser clean off.

Dustin Smith - 2017-11-04

We want to see the failure regardless! Or atleast add it onto the end of the success. :)

Yata Garasu - 2017-11-04

igext because its grignard

Daniel Austin - 2017-11-05

did you add a crystal of iodine?

spiderdude2099 - 2019-01-26

chemistry500 there should be a reaction but it may have a much lower yield and take much longer. The sulfuric acid makes the run go way faster. HBr is a stronger acid than HCl which is good, but it's still not great. Not sure but ethanol plus HCl may not react at all or even worse than HBr and ethanol. You can make chlororethane using HCl, HBr, or HI and sulfuric acid but not sure if you can get away with no sulfuric acid at all

eivilcow - 2017-11-04

6:35 This made me laugh way more than I should have. You are normally so careful about adding things, and you just threw the Anhydrous Magnesium Sulfate so haphazardly.

Dustin Smith - 2017-11-05

And casually just moved along without mentioning it. Haha. I laughed hard. I was expecting him to drop in a hand full after that.

Eric h - 2018-06-10

I had to pause the video and look for the inevitable mention of this incident. I cracked up hard at that, it was like the moment Nurd Rage suddenly turned into How to Basic LMAOOO

Chuck Vanderbildt - 2017-11-04

Your H2SO4 looks disturbingly brown even for drain cleaner standards! Maybe try another brand?

piranha031091 - 2017-11-04

Or you can warm it up and add a few drops of hydrogen peroxide to it to oxydize the carbon into CO2. Basically making piranha, but with very little peroxide, ideally just enough to consume the carbon. (though doing so may leave some residual peroxide behind and water down the acid a little)

borttor MCPE - 2017-11-04

If I remember correctly it had some Organics or it was the dye that was used in it

GRBTutorials - 2020-02-05

piranha031091 Or just heat it up. That should be enough.

Gravelle Art Studio - 2017-11-05

I like this video, no bromo

lightvsdark21 - 2017-11-04

Are we starting a new series?!?! Yay!

Aussie Chemist - 2017-11-04

The first experiment seems to be done in a professional lab.

Michael Evans - 2017-11-08

Going to use this in my Organic I course in the spring! Thanks, NR!

Udathiocyanat - 2017-12-03

Hi! I am an amature Chemist. Could you please make a Video about how to reach the theoretical yield?

MrTuohitorvi - 2017-11-04

I've been thinking about bromine burning reactions. How much does the bromine being in a salt compound affect it's oxidation process? Is there a difference really at all?

SoulShak3n - 2017-11-06

I like how you left the stir bar in lol

Zzyzx Fox - 2017-11-04

Thank goodness you uploaded, not only are you one of my favorite YouTubers but I finnaly see a new video that isn't about the iPhone X

Chris Booker - 2017-11-04

When you finally start understanding what nurdrage talks about after taking Organic Chem 1

Tyt0uOff - 2021-01-09

Can the second method be used for the first reaction ?

eternalights - 2017-11-08

thanks to the reminder bell i was able to watch this. once again you are not showing up in my sub box. it seems that only every other video comes threw.

EUDIS FLORES - 2017-11-10

Make a video on how to take metals to mono-atomic state pleasesss😀🤗

nerdalert226 - 2017-11-05

I loved the fact that I am finally in Organic Chemistry I and can follow the procedure perfectly. Being a chemist is awesome.

ScienceWithJames - 2017-11-05

6:35 Good job

K T GaMeS - 2017-11-06

hi there i want to get my hands on some gallium but i herd that it is super expensive and i can find to buy any ideas

TheGinginator14 - 2017-11-04

Great video man!

Josh Spurgers - 2017-11-04

I wonder why that one wise guy decided to downvote the video. Probably saw "Bro" twice and was disappointed when he found out it was chemistry.

wazscience - 2017-11-04

i remember making this stuff in my organic chem class

Entenkommando - 2017-11-04

Yeah I think I made bromohexane in the lab.

ᴠᴧᴨᴛᴧᴃᴌᴧcᴋ - 2017-11-05

I made this stuff on paper...

Lukáš Stibůrek - 2018-05-08

Hello, I want to ask whether this is in the manufacture of bromohexan used instead of sodium bromide potassium bromide? and if so, in what amount?
Thank you ;-)

ProCactus - 2017-11-06

You sound very different in this video.

Ciencia Quimica - 2017-11-05

Another Great video !! :D :D -- Mm ... Diferent lab's ? :/

Garo Nadjarian - 2017-11-04

101 view

Chemistry Guy - 2017-11-05

My first gringard went out of control and boiled over... so I'm pretty sure you did better than I did!

Michael Chauncey - 2017-11-06

Question: Do you think a gentle reflux for a few minutes would increase yield?

Gerko - 2017-11-05

Greetings fellow nerds. Today I'm going to show you how to make hydrogen oxide. Before we begin I'm going to crush your expectations. Creating this isn't cheap than buying ordinary H2O at your local store. We're doing this to explore the science.

Bon Bon - 2021-01-08

Then how is it that those companies can produce tons of those chemicals and it's affordable for them , and yet somehow the same is not affordable when you try the same? :q

PickledSoul - 2017-11-05

what are those red things on the condenser?

axel boström - 2017-11-04

This one of those channels you probably should download and archive for the nuclear apocalypse, so much useful info

munitiondragon69 - 2017-11-04

do you think it would be a good idea to show the moles of substances whenever you are showing how much you used? might be a useful thing for viewers to know without having to figure it out themselves.

Yata Garasu - 2017-11-04

if you want to follow his recipe u dont need the moles. The only ones who would need moles could easily calculate it themselves

MisterGee Marino - 2017-11-04

Will this procedure work to make Dibromo compounds from alkyl diols? Say... 1,5-dibromopentane from 1,5-pentanediol?

Todd Decker - 2017-11-07

Please make sure your content is also stored at an alternative site in cause your caught up in issues similar to Cody’s Lab

Alan S - 2017-11-04

That's a lot of magnesium sulfate, lol!

Léon the Professional - 2017-11-04

Grignard reagents! FINALLY!!

a - 2017-11-05

How the hell did you get that bitcoin address?

Daniel Austin - 2017-11-05

now you could convert them to alkyl iodides by refluxing with sodium iodide in acetone

Stanley Nicholson - 2017-11-04

Can someone please send me the link for the photo reaction he mentioned in the video? Thanks

NurdRage - 2017-11-04

whoops, my bad

Stanley Nicholson - 2017-11-04

Thank you very much and keep up the great work!

aciddaddy420 - 2017-11-05

That's a pretty complicated process. Any chance of a How To Basic method?

Annisa Nur Khaeruni - 2020-01-31

is it okay if i use a secondary alcohol? like 2-hexanol

Hardik Mhatre - 2017-11-05

Hii I am Hardik can we follow the same procedure to make chlorotoluine by using hydrochloric acid or any kind of chlorinated hydrocarbon ??

AlucardPawpad ClownWorld - 2017-11-04

By the time I need to use this knowledge I'll forget it. By the time the times make such circumstances where one needs to know this information, this video would be taken down because it's anti-gov. Hnnn.

Bon Bon - 2021-01-08

Download it to a local backup copy. That's what I do. Then you'll still have it when you need it.

frederik Petersen bach - 2017-11-10

Hi there Mr Nurdrage, 1 year ago you asked us to ask you about how your hotplate stirrer elements has been doin, so how have they been doing?

FZR650 - 2017-11-05

Make some whisky!

Kaiser Andrenius - 2017-11-05

Is there a reason why you aren't doing this with the Appel reaction?

mozarellaman1201 - 2017-11-05

Andreas Müller because triphenylphosphine is hard to obtain for the amateur as is carbon tetrabromide, which is also toxic

piranha031091 - 2017-11-04

Where did you get the hexanol from?

OpiatedBliss - 2017-11-07

Are you sure you don't have the 2-bromo hexane?

NurdRage - 2017-11-08


science_and_anonymous - 2017-11-13

is this also how you would make chlorobenzene except with a chlorine source?