Making a Bromoalkane (1-bromopentane)

[@zakstamaj]

I am so glad that you produce chemistry videos... because people like me don't have the equipment at home to do chemistry. So I an filled with grateful feelings that YT exists... and that NileRed exists.

[@starlight4649]

When you accidentally touch your bro's test tube you have to say no bromo.

[@Gojojojojojo]

🤣

[@jaken1319]

Lmaoooo no cap

[@FranktheDachshund]

Haha clever!

[@jaken1319]

😂😂😂

[@jaken1319]

Back again!!

[@Eugene-fh6zp]

Hey nile, been watching a long time. Inspired me to get into chemistry. Today my teacher told me to watch this video to practice on taking lab notes. Feeling good cause i can always understand you

[@jayr4485]

Thank you for the really cool videos!!! Please keep this up!

[@rem520]

Just had this video as part of an assigned lab worksheet for O Chem, was super cool to get a grade based off content I watch for fun :)

[@elleeVee]

Things that don't smell nice? Make some damn Thioacetone. Do it. Bet you won't.

[@DeanBiddler]

Bet you won't smell hydrogen sulfide until you can't.

[@mr.youtuber9602]

yeah a chemical that has been known to caue city-wide evacuations because a chemist spills less than 10 milliliters of a sample I wouldn't touch the stuff either

[@Madarpok]

Try to make selenophenol.

[@alphatks]

Why don't you make it! And Post in KZbin!

[@U014B]

Now I want to know what VFDF smells like...

[@NileRed]

Here is the more detailed link: kzbin.info/www/bejne/ooiphYyHYt1gia8 Sorry guys, it slipped my mind!

[@parasdsingh]

Awesome stuff! Loved the details

[@MisterLepton]

Have you ever attempted radical bromination of an alkene with the ultraviolet peak from a mercury vapor lamp? I’m curious how long it would take with a 120V/175 W bulb. Just as a subjective judgement this thing puts out A LOT of UV. I suppose I could calculate the approximate time. But it’s 8 o’clock in the morning and that’s a lot of calculation with a lot of variables.

[@TheFacedGAM]

Will not lie, I'm very excited to see the synthesis of caproic acid.

[@travisheck5979]

"what does that chemical smell like man?" "it smells like... GOAT". "what.."

[@Dra9ontail2]

Well.. at may be weird to think of a smell that is specific for goats, but I can tell you from experience, Caproic Acid REALLY smells like sticking your face into a goat's fur. That is the most accurate way to describe it. It's awful. I use it at my job :P

[@mauz791]

@@Dra9ontail2 Amazing! You ever thought about putting a little on an irritating coworker?

[@maggiep9007]

@@mauz791 I did that to a girl I used to work with for revenge. It backfired and she married a handsome Arab fellow.

[@mauz791]

@@maggiep9007 that's some amazing wordplay. Nice.

[@luisp.3788]

@@mauz791 Late, but caproic acid is toxic on skin contact, so I would not recommend.

[@brianreddeman951]

11:30 Epic moving shot LOL :)

[@512qwerty1]

Doesn't 1-bromopentane (or any alkyl halide) undergo an SN1 reaction with water to form an alcohol and the corresponding halogen acid? Could that side reaction be the reason for the lower yeilds? Ex. 2-bromopropane + H2O ----> isopropanol + HBr ?

[@NileRed]

To a certain degree it does, but the rate should be quite slow (as far as I know)

[@lukassorowka2672]

Isopropanol definitely doesn't form lol

[@rehanmohammad5841]

​@@lukassorowka2672😂😂😂😂

[@Sandymouseguy]

I have a bottle of caproic acid. It stunk up my whole closet of chemicals. But it doesn't smell that bad. It just smells like cheese, just the smell is so strong. You can even use caproic acid in other reactions too. I used it in a freidel-crafts acylation with PCl5 ACl3 and benzene to make hexanophenone.

[@brandontolon7111]

awesome video, you make everything seem real easy lol

[@LordSparkleBottom]

Those pouring skills are too good

[@benlucas1039]

That was the GREATEST moving shot!!! Nice work, keep it up. . . . . . . And nice pouring skills.

[@MedChemist1]

My guess for the low yield would be that you did quite a few washing steps that were in all honesty, unnecessary. I'd wash with water, then bicarb then dry and distil, skipping washing with acid because you are distilling anyway. plus using a column in the distillation was overkill IMHO, if the difference in bp were a few degrees then yes use a column, but with a bp difference of 70 degrees there is no need for a column. Of course I have the benefit of hindsight :P 60% is still a decent yield especially for a first run using a new method, I've cocked up much worse lol. Out of curiosity, why did you use sulfuric rather than phosphoric? where i live it's much easier to get hold of phosphoric as a aquarium/pool chemical than it is to get my hands on conc sulfuric. just curious is all.

[@nicholi8933]

I saw your reagents and my first thought was he is doing an Sn2 reaction.

[@captainchicky3744]

the yield was low probably because making HBr in situ still means you have H2So4 left, which likely did E2 on the alcohol and formed an alkene. Then, HBr attacks the alkene and forms 2-bromopentane, which has a consideraby lower boiling temp than 1-bromopentane. I'd suggest to anyone who tries this to actually make the HBr first, and then use the purified HBr to conduct the SN2 reaction.

[@theginginator1488]

How about a video on making 1,3 dibromopropane, the precursor to cyclopropane

[@arnaud2646]

Nile, could your yield be low because you used a too strong heating, thus favouring the elimination instead of the substitution ? Did you get any product around 30 °C ? Great video, love your stuff.

[@theodionne9370]

Clicked on the video thinking it was nurdrage, almost thought it was a voice reveal.😰Oh well, still enjoy your work Nile!

[@nemeanlyan7918]

Nile is better than NurdRage tho.

[@brianlyao]

What do you mean by better?

[@krisztianszirtes5414]

+Brianlyao Well to be honest, Nile Red has a nicer quality of production and camerawork for one. I really like the flat colour backgrounds here. Then there's the frequency of videos. Also, that voice changer started becoming a bit annoying. Like 50% of the time I needed the subtitles for a few parts. And then there are videos by nurdrage like "How to light a bbq like a chemist"

[@brianlyao]

Krisztián Szirtes I definitely agree with a lot of that, especially frequency of videos and quality of production; I was just worried that he was comparing them by chemistry experience/skill/etc. which wouldn't be a matter of opinion. I wouldn't give him too much flack for that bbq video; I think Nile made a similar "for fun" video with turkey or something? Anyways, it seems chemists like to have fun too. :)

[@ThePaintballgun]

You should look into making one of the patreon tiers a beaker with your logo on it. I don't know if it could be done, but it seems like it would be a cool bit of swag.

[@NileRed]

That is actually a pretty cool idea. I was tempted to get into merchandising of sorts, but I had no idea where to even start. Ill put a little more effort into it though.

[@a3xccy379]

Epic Moving Shot and Godly pouring skills that crackedit up !! Synthesis of paracetamol or quinine ?

[@gsurfer04]

Wouldn't conc. sulfuric acid dehydrate the pentanol to pentene?

[@HiddenAnon226]

gsurfer04 idk if you’re still concern about this after a year but an elimination reaction will not occur since HBr will be formed before the addition of the alcohol. Once the alcohol is added the SN2 reaction will occur faster. And as he mentioned that NaBr is more soluble which means the NaSO4 will precipitate out.

[@peterectasy2957]

yes, but less than 1 %

[@jessekalahar417]

I’m searching through his videos trying to pinpoint the exact point in time when he begins talking in his iconic voice.🧐

[@Harmonikdiskorde]

Separatory funnel: the chemist's gravy separator

[@xenomancer1]

You could try some xanthine derivative or ionic fluid syntheses. Also, I've made some fun esters of citric acid like (mixed) menthyl citrate(s) and polyvinyl citrate. Menthyl citrate smells like a zesty orange and polyvinyl citrate is quite viscous. There's a rich and aroma rich chemistry to menthol/cresol/cinnamaldehyde reactions that may be some fun. Also, the conversion of acetone to pinecolone is nifty and can be done in a variety of ways. Simple distillation over sulfuric acid should be sufficient.

[@rogerandlyndabeall3840]

I make haloalkanes by (say kerosene) heating to about 90C and bubbling chlorine in directly. It will absorb chlorine until it looks like wax and is 70% Cl

[@DUIofPhysics]

Since you are doing Red P from matchbooks, will you be doing KClO3 from match sticks?

[@EvelynnEleonore]

Could you oxidize the NaBr? NaBrO

[@StefanReich]

KBrO

[@kadergumus2598]

Hypobromites would be hard to make.

[@mauz791]

@@kadergumus2598 read the chemical name carefully.

[@kadergumus2598]

@@mauz791 Nah Bro - I understood the joke. K Bro would be Ok Bro.

[@mauz791]

@@kadergumus2598 sorry about that!

[@raiyiar]

Hi! Big fan here :) I just wanted to know if you could use this mechanism for polyols as alcohols, e.g. glycerol (propane 1,2,3 triol) or propylene glycol (propane 1,3 diol) to form 1,2,3, tribromopropane or 1,3 dibromopropane, and in case this works for these, in what order would the OH-groups be swapped for Br? And lastly, if i used a stoechiometry of 1 alcohol to 1 Br, would i receive mainly 3-bromopropan-1-ol with PG, or would the 3-bromopropanol be more reactive and tend to grab the second bromine? and what would be the main product of the reaction with glycerol?

[@pietrotettamanti7239]

The 2nd carbon would be the first. Generally secondary (and tertiary) carbons are more reactive than primary ones in electrophilic substitutions or additions. Though I don't think that 1-2-3 bromopropane would be very stable because of steric reasons (propane is a fairly little molecule while bromine is really big compared to it, and therefore there would be a great tension).

NileBlue has forgotten this sentence in early 2022... "As some of you might know, I'm pretty big fan of things that don't smells very good" 1:29-1:34

[@jacogomez1093]

i was thinking the same

[@115Carssssssssss]

High-school-students-friendly content

[@nilnileer]

yes

[@seilgu]

What happens if you replace the Br with Cl ? Use HCl to get chloropentane, and then use grignard reaction to get the MgCl reagent ?

[@shodanxx]

Can you talk more about molecular sieves ? Where do you get those things ? What can they do beside remove nitrogen from air or capture moisture ?

[@heathrouette1069]

Might be a bit late on this hahaha but eBay has them. I think it's like activated charcoal but it's made from zeolite, but I could be wrong

[@kkirschkk]

more! do even more!!!

[@lemmerelassal610]

When you don't know which layer is which - just taste them. Water tends to taste watery.

[@caseybaker528]

squirt water in and see which layer gets bigger :l

[@jacogomez1093]

@@caseybaker528 Done that way too many times to be honest

[@rollaroundaparty]

Is there a link in the description for the more detailed video? :D

[@NileRed]

+rollaroundaparty ah man I forgot. Also I am away right now so I'll update it when I get bsck

[@flaplaya]

Ah shucks. The Patreon link is front and center though.. Maybe next time :) Great substitution to the Highly reactive Bromo Alkane here.

[@rollaroundaparty]

It's alright :D Looking forward to it

[@NileRed]

I edited a few videos and totally forget when I say Ill include stuff in the description! It's bad. I should start writing it down.

[@xelionizer]

We're only humans

[@cobalt7530]

Could I use this reaction for making dichloromethane by combining twice the moles of sodium chloride and sulfuric acid used in this video with formalin (80% of the formaldehyde in aqueous solution is hydrated to methanediol)?

[@stephenjacks8196]

One product is bis-Chloromethyl ether a powerful DNA alkylating and cross-linking agent.

[@_general_error]

This looks like it would work on all primary alcohols. What about substituting NaBr for NaCl? Would this resolve in chlorination?

[@lukassorowka2672]

Yup, but bromination is more favorable(higher yields)

[@tarrySubstance]

why cant we use UV light to speed up the reaction?

[@azice6034]

Hamza Rauf rxn is already fast enough

[@james1458256]

Could this approach be effectively modified for ispropyl iodide? What kind of yields could I expect?

[@Progamezia]

No.Sulfuric acid creates elemental iodine in its reaction with iodide salts,instead of hydroiodic acid.Your best choice would be to make isopropyl bromide and then do a Finkelstein reaction with NaI.You can find more info on Wikipedia

[@DeDraconis]

Are the 1-bromopentane and 2-bromopentane handed molecules? Just wondering if 3/4 pop up if the Bromine molecule keeps moving down the line.

[@DroolingYeastman]

Suggestion: Vanillin

[@ssb492]

How do you choose your drying agent? Is there a paper, that gives you an idea or is it just a feeling you have?

[@blueknight3221]

There is no such links in the description as you promised!

[@nthicidea5138]

Mercury from Mercury Sulfide/ Cinnabar

[@vrowniediamond6202]

when he says a "simple distillation"... It just makes me feel kinda bad because i can't even do that.

[@pietrotettamanti7239]

Vrownie Diamond it just means "not fractional". There are 2 main types of distillation and are "simple" and "fractional".

[@caseybaker528]

@@pietrotettamanti7239 Well I mean vacuum and ,to an extent--steam, are also big ones. But in general yeah. "Simple" just refers to standard distillation with no other modifications to assist separation other than basic vaporization and condensation

[@Thebarnardfactor]

Nile I have to ask, is there any Economic Incentive to pursue a major in chemistry

[@DeanBiddler]

I think you are looking for justification to go into a business major.

[@Thebarnardfactor]

How did you know?

[@DeanBiddler]

You said the words economic incentive. . . . . .

[@ExpiredCartonOfEggNogg]

Like as pay? Or as a buisness?

[@BackYardScience2000]

Not really. Chemists aren't paid all that well. Generally $20 - $30 an hour depending on where you decide to get a job. If you could synthesize a new compound and profit off of its sales, maybe. If you do it yourself instead of for a company that is. But seeing as most of the easy compounds have already been synthesized, it would be more work than it is worth unless you really want to just contribute to science. Here is a chart showing the average pay, both hourly and annually per state in the US. I fall a little lower than midway of this scale. The really high paying jobs are usually the ones that deal with more dangerous substances. Which also brings up the question, am I willing to take that risk to make that good of money? www.ziprecruiter.com/Salaries/What-Is-the-Average-Chemist-Salary-by-State

[@nuclearthreat545]

good video brother

[@fpuGermany]

where do you get your synthesis instructions from?

[@tannernolan]

Diisopropylphenol synthesis?

[@googleeatsdicks]

sponsored by Conrad Murray

[@batsman46]

okay i see why its SN2 in some regards but are the conditions not polar protic?

[@TheAlexagius]

So are you going to do/have you done a video on the nile red method?

[@stonent]

I have not used Pentanol before, wikipedia says it is known for its unpleasant odor, and I was curious what that was like. Most alcohols that I've used, ethanol, methanol and isopropanol all pretty much smell the same.

[@NileRed]

The smell isn't terrible but I honestly dont like it very much. Not sure how to describe it though

[@sirgooogen]

when making secondary bromoalkanes, I have problems with charring during distillation and sometimes on the addition of the alcohol. Is a different technique used for substitution of secondary alcohols, especially in longer chains?

[@eliduttman315]

Primary alcohols undergo almost exclusively bi-molecular nucleophilic substitution. Tertiary alcohols undergo almost exclusively uni-molecular nucleophilic substitution. Secondary alcohols undergo substitution by both necleophilic mechanisms. Perhaps both mechanisms being active had something to do with the charring or too much H2SO4 was present. Was vacuum distillation, to reduce the temperature needed, considered? The neopentane (tetra-methyl methane) configuration is "unusual". Neopentyl alcohol is primary, but it is sterically hindered. Think tert-butyl methanol.

[@phallusaurus]

would you be interested in doing the reduction of vanillin to vanillyl alcohol?

[@shanchilla]

Can kalium bromide replace sodium bromide ?

[@Spycyzygy]

yield is probably low from water present hydrolyzing bromopentane back to pentanol

[@pietrotettamanti7239]

Rsaramallac nope, OH2+ is a much better leaving group than Br-. The equilibrium should be far towards the products.

[@morganguest9360]

Can you explain how you calculated for % yield? What was the limiting reactant was it the H2SO4?

[@wilms2328]

A reaction like the one is this video is basically the bromide kicking the alcohol (OH) out of the molecule. The H2SO4 serves to protonate the alcohol (turn OH into OH2+), which makes it possible for the bromide to kick it out. He probably used an excess of acid to make sure the alcohol became as protonated as possible, which would make the bromide the limiting reagent here.

[@harrylatka1]

Sorry if this is an obvious question, but what is that little spinning pill at the bottom of the glass?

[@xxsebasalxx]

It's a magnetic stirrer

[@MostFolkCallMeOrangeJoe]

It's a stirbar. Basically a small bar magnet coated in Teflon (Or sometimes ceramic/glass). The flask sits on a hotplate which contains a magnet on a motor.

[@alrx461]

I GOT LINKED TO THIS for a school assignment AHHAHAH

[@jaromschafer913]

where did you get your n-pentanol? i would like some to make molecules like this.

[@wubwub616]

Me: "do I get anything else than methanol when I mix natrium hydroxide with methyl hypobromite?" NileRed: "NaBrO"

[@plazmotech5969]

natrium? are you German?

[@wubwub616]

@@plazmotech5969 yea I realized it myself after :D

[@nilnileer]

Sodium

[@serb174]

At 14:12 - What's AlumOnum Isopropoxide?

[@alex92569]

Typo. Don't be a smart alec.

[@serb174]

Alex Petrov I know what it is but just sounds weird. Try and say it out loud while being serious.

[@anthonylepore516]

This question has nothing to do with this subject, but damn it I can someone please tell me if instead of mixing H2O with calcium Carbide, I use D2O , will the acetylene have more cutting power??? I don’t want to waste money on heavy water just to end up feeling like a donkey!

[@grebulocities8225]

No, it should have pretty much exactly the same cutting power as regular acetylene. If anything, very slightly less if there's a kinetic isotope effect, but it's probably pretty negligible. Reacting heavy acetylene produced this way might be an interesting way to make deuterated compounds though.

[@bbrockert]

Why are glass column stills so sparse inside?

[@adamlifevictor5772]

So, there is a lot of HBr dissolved in the aqueous layer. Not very surprised actually.

[@joshuad007]

Please try to do all reactions given in Indian NCERT Class 11 Hydrocarbons.

[@stephenjacks8196]

Phosphoric acid doesn't oxidize HBr to Br2

[@XXLSkinnyMcGee]

you should get a black background when you're performing organic chemistry 👽👌

[@Rubikorigami]

Skinny McGee wut?

[@HGPOfficialGaming]

Organic chemistry tends to be white or very dull colors, having a black background would make it easier to see changes is what he's trying to say I assume.

[@deblobvis264]

He already has that

[@SodiumInteresting]

Did you even watch it 😳

[@HGPOfficialGaming]

@@SodiumInteresting I did yes. Was just clarifying what I thought was said.

[@Ostenmaster122]

Can the same be done with sodium chloride?

[@NextGenAge]

Doesn't the H2SO4 washing step convert some bromide to bromine?

[@mr.youtuber9602]

I believe it's because concentrated sulfuric acid by itself is not a strong enough oxidizing agent to oxidize the bromide ion need something to help oxidized it such as H2O2

[@NextGenAge]

+Mr.KZbinr I saw some guy on youtube convert hydrobromic acid to bromine with addition of hcl.

[@darkzone2709]

Hi you could do a video on how to do trinitrotoluene

[@keondrewalker5415]

Learning is fun

[@JoshuaRando]

Why does being around hydrochloric acid cause your nostrils to burn? Is this bad to happen?

[@Rhodanide]

LMAO

[@stonent]

As a kid I was playing with some HCL that my dad got for some reason and tried dissolving pennies in it. I decided to take a whiff and WHOA! that will wake you the F- up!

[@Rhodanide]

stonent Yeah, try Chloropicrin.

[@stonent]

I think I'll leave my sinuses alone for now.

[@Rhodanide]

+stonent safe bet.

[@siberianstuntman3344]

What are the guidelines for choosing a halide?

[@stefangadshijew1682]

If you substitute with iodine, you get a very reactive alkyl halide that is easily substituted. Alkyl bromides are usually sufficiently reactive. Alkyl chlorides are, depending on the reaction you are doing, the least reactive and sometimes require harsher reaction conditions. On the other side, iodides and bromides tend to have side reactions going on and may lead to a discoloured product. Also, alkyl chlorides are much more affordable and sometimes less toxic. Very often, the affordability of alkyl chlorides justifies lower yield, longer reaction times or harsher reaction conditions by a large margin. One very convenient way to do substitutions with alkyl halides is the Finkelstein reaction. You can substitute a chloride with an iodide in some organic solvents like acetone or THF. Usually, iodide would not substitute chloride quantitatively, because iodide is the better leaving group. But since sodium iodide is quite soluble in acetone while sodium chloride is not at all soluble, the precipitation of sodium chloride drives the reaction forward. Very often, it is sufficient to add tiny amounts of iodide, in the ballpark of 1 mol% to 5 mol%, to significantly speed up a reaction, since the iodide ion is regenerated in a subsequent substitution. R-Cl + NaI (dissolved) --- Acetone ---> R-I + NaCl (precipitate) ---- + Nu(-) ----> R-Nu + I(-) So to answer your question: 1) You start with the alkyl chloride. If that doesn't work: 2) You try the Finkelstein Reaction. If that doesn't work or turns out to be messy: 3) You try the bromide or the iodide directly.

[@KingNast]

Can you make skunk odor?

[@jakep519]

So did you get your strike resolved?

[@rogerdotlee]

You're getting quite the following these days. I guess all I really ask is that you don't close up shop like Chem Player did. I need a somewhat regular chem fix. How difficult is it to make the other variants of bromopentane?

[@officialninjachannel]

Where did you learn chemistry?

[@U014B]

When you said caproic acid didn't smell good, I thought you meant like feces ("kopros" being Greek for poop), but then I remembered that chemistry was invented by the Romans or something, so obviously the Latin "capra" (which means "goat") was in view. ...or I figured it out only after you said it, so I looked it up to make sure.

[@maggiep9007]

I think Latin persists since its use means most people understand the words, even if they don't speak a latin-based language.

[@maggiep9007]

Plus I think the origin of chemistry is decentralized. Paul of Taranto wrote his alchemy in Latin, but used the pen name Geber, the latin form of Jabir (Hayyan), a Persian alchemist who spent much of his life in Arabia.

[@Irongolem27]

By the time you finally synthesis Octen-3-ol, summer will be over so you won't be able to test it X)

[@montanalivin8248]

Do some hexane videos...

[@MohammedMohammed-eb2yk]

How I get bentanol

[@rogerandlyndabeall3840]

I asked if you were making Sodium HypoBromite you said NaBrO

[@evilotis01]

booooooooom

[@puppiesarepower3682]

BRO🤜💥🤛MINE WE🤝BRO!

[@pvc988]

At 8:17 what is that fire looking reflection at the bottom of the flask?

[@pvc988]

Ohh… I am dumb. It is probably that you are using a flame to heat that stuff xD

[@appledream8573]

Can I use any sodium halides

[@maggiep9007]

I also want to know. Why not chlorides or iodides? Are these much less practical?

[@Albot1288]

Hey can you do a video on organic chemicals like norepinephrine?

[@dannyboy12244]

Albot1288 errr this is an organic chemical are ready. Why norepinephrine?

[@NicolasBana]

Wanna make all alarms sounds and evacuate people kilometers around ? Make Methylmercaptan (methanethiol) !

[@clarencek3658]

Just seeing if someone made the "NaBro" joke yet

[@Techtradragon]

I was wondering how he was gonna nullify the inductive effect to add the bromine to the end of the pantene chain... and then he pulls out pentan-1-ol loool

[@parmavioIets]

my chemistry teacher is making us watch this video and fill out a four page worksheet someone kill me now

[@marinogarym]

Would this reaction work with a Diol (to make a dihaloalkane), as well?

[@marinogarym]

It would be nice, if you'd answer my question... :/

[@hachikiina]

hello darkness my old friend

[@stephenjacks8196]

Diols plus acid can yield aldehydes and ketones

[@beanny39]

Yeah, science.

[@godfreypoon5148]

I got motion sick.

[@quoverlord9398]

Fluorine best Halogen