Making the Smell of Rain

[@Chemiolis]

Finally it's here!! For full transparency, during one part of the project my SD card corrupted, causing me to lose some footage. Since I couldn't go back and redo it, I had to record staged footage and reuse older footage. So from 19:45 to 20:58 and 21:40 to 22:17 you see me re-enact what it looked like as closely as possible but without the product actually being there. Then from 20:59 to 21:39 I am reusing footage from before. Also, the structure of m-chloroperbenzoic acid at 17:44 is drawn wrong, it should be the meta isomer, not para. And I realized 'cyclisize' is not a word, I will use the excuse of not being a native speaker. Enjoy this 11 step synthesis!!

[@Coffeesleep125]

New minion movie looking good lol. great work very impressive

[@adrianpip2000]

Extremely cool multi-step synthesis! Not to mention that you did some high quality practical synthesis here. Also pretty cool that you're sending off samples to supporters. Would just like to add that it'd be nice to have some small text in the corner of the video when it's a re-enactement. Cheers!

[@shiftgood]

1ml of this sells for $360....

[@joshuaosterhout]

This content was super interesting, but it comes at you like a bullet train (no pauses). It can be a little disconcerting when you speed through 5 solid minutes of chemical names with no break in between.

[@cas8891]

Are you by any chance dutch? I noticed a little bit after way too long but i did pick out a couple of pronunciations when i started to focus on it, and now you saying youre not a native speaker... That would be really cool! Anyways loved the video im glad i got it in my recommended im definately gonna binge you

[@kiro9291]

there's nothing quite like finding a new chemistry channel to binge

[@oldboyneverrichagain1113]

rightt

[@shebahammy]

When Nile red is taking too long

[@jc4359]

This is my first video of his too, I'm 45 seconds in or so lmao. Already know I'm gonna be watching more.

[@spyingpro4563]

@@shebahammy haha yes 😂😂

[@udittlamba]

I just found this channel and I concur!

[@joaogabrielaguiar3761]

In the beginning of 2020, a large chunk of Rio de Janeiro's water supply was contaminated with geosmin due to an cyanobacteria* bloom in the Guandu river, from which most of Rio's water is pumped. There was nothing wrong with the water, it is obviously treated, but they couldn't remove all the geosmin, and since we can detect it in such small quantities, everyone's water tasted and smelled like dirt for some months. It still happens from time to time, but it usually lasts a few days, nothing compared to the almost three months (iirc) in 2020. * Although Brazilian media just called it an algea bloom, cyanobacteria aren't algea.

[@abacaixi]

Todo mundo gosta de água do filtro de barro, mas quando a água fica com gosto de barro todo mundo NOOOOOSA

[@ygdbll]

@@abacaixi pior

[@feliscatuzz]

hmm delicia agua com cheirinho de terra

[@2ndPortal]

You're telling me instead of synthesizing it we xan just get some algae to do it for us? Lol

[@LukaFanNo8]

was there ever a paper published about the type of algae??

[@pezboy715]

17:03 you know you’re not feeling great about your yield when you suddenly feel the need to add a decimal

[@Knot-orious]

Officially the best comment. This is so real. =-D

[@EddieTheH]

"after 100 years, it has all filtered through" We're all familiar with that! I do enjoy that anhydrous humour.

[@autisticguitar666]

Interesting last name Eddie

[@EpicManaphyDude]

anhydrous humor 😂

[@EddieTheH]

@@autisticguitar666 Give it a Google, you might laugh.

[@_Solaris]

Clever.

[@jixpuzzle]

"Anhydrous humour" nice one lol. Only chemistry students will get it haha.

[@leek5682]

Can’t get over how complicated this process is. In my college organic chemistry labs I’d manage to mess up a 3 step process, so seeing someone carry this out so perfectly is super impressive.

[@zachliveris2881]

Yeah but the chemistry has been done before. A 3 step novel synthetic route can be far more challenging vs repeating known procedures

[@naumen6508]

​@zachliveris2881 you think they did novel synthetic routes in college ?

[@isocle]

"In the end, I am left with.. YELLOW???" What a plot twist haha! Tom really did the chem community right with starting this trend

[@T3sl4]

Chemtubers all watch each other and I am here for it

[@hashimhassan4970]

Wait can you explain the yellow trend and where it started?

[@T3sl4]

@@hashimhassan4970 Extractions and Ire

[@isocle]

@@hashimhassan4970 Tom from explosions and fire (and his secondary channel, extractions and ire) has a running gag of yellow = bad after having a terrible experience trying to make S4N4, pretty sure. Since then it's kind of picked up because most of the time something going yellow is a bad sign that something is degrading and tar is coming your way :)

[@oufannamedbrandon6715]

​@@isocle also Grimace isn't yellow.. Don't forget about Grimace now! The ol' goofy purple bastard!

[@craoun6116]

As a preparative organic chemist I have to say, that is some quality work right here. Congrats to you my friend, I usually mess things up big time when trying to reproduce a paper for the first time :)

[@defenestrated23]

As a (former) synthetic chemist and longtime chemistry hobbyist, I concur! This is great work.

[@antares8826]

Videos like this always make me appreciate the rotary evaporator we have in our lab.

[@ghislainedidntkillherself]

you got any broken out-of-service units? asking for… a friend of course

[@zachliveris2881]

​@@AndyU96 they both accomplish the same thing except the vacuum distillation setup in the vid applies heat which can be bad if your compounds are sensitive to heat. But mostly cause it takes way less time to use a rotovap vs using vacuum distillation

[@2bleubird]

@@AndyU96rotovap is faster and easier to get going.

[@oitthegroit1297]

That's my favourite smell, along with the smell of pine trees and cool, brisk, fresh winter air, as well as burning wood. Just writing this brings back so many memories, it's surreal.

[@jackass6257]

I feel like the morning summer air of the suburbs with all the pine bushes and trees, but here in Cali winter is the best if you have a clear nose cuz everything is blooming after rain

[@garycard1456]

I wonder why the air on a crisp frosty winter morning has its own characteristic smell? What could the chemical composition be?

[@oitthegroit1297]

@@garycard1456 The chemical composition is 78.08% nitrogen, 20.95% oxygen, 0.93% argon, 0.04% carbon dioxide, small amounts of other gases, and 100% cold lol.

[@ghislainedidntkillherself]

@@oitthegroit1297 sounds about right. checks out👍🏼👍🏼👍🏼

[@MrCh0o]

​@@garycard1456 I always thought it was just the nose getting instantly runny causing the "smell", since it doesn't seem likely that there's anything special in the air during winter

[@KetamineKakarot]

As our Aussie friend always says, yellow chemistry is evil lol

[@schr4nz]

And our Canadian friend says "I love urine chemistry!"

[@crabcrab2024]

To be honest, I am really sick and tired of this. Yellow is just as good as the other colours of the rainbow.

[@_thisnameistaken]

@@crabcrab2024 yellow is a bad color🥶🥶🥶🥶🥶

[@jaymzx0]

Tar!

[@crabcrab2024]

@@jaymzx0 Tar is dark-brown or black, not yellow)))

[@pelegsap]

Regarding 13:23 - I'm sure you already know it, but for anyone who wonders: many organic stuff are yellow because they have a lot of conjugated bonds in them (in the case of the imine here the bezene ring is conjugated to the nitrogen via its free electron pairs). This causes the electronic excitation energy to drop, bringing it from the close UV range into the visible range, i.e. the molecule absorbs deep-blue/violet photons, and we're left with a yellowish-looking product. For green we would need to absorb in the visible range both blue and red, which is not very likely.

[@T3sl4]

In addition, the aldol step at 15:45 tends to produce anything from yellow to orange, red, brown and tar -- at least on less, specific shall we say, substrates? Example, a similar reaction done with acetone leads to condensation products ranging from diacetone alcohol to mesitylene and relatives, and onward including indeterminate polymers. Fortunately, the molecule here reacts preferentially with itself in good yield.

[@waterunderthebridge7950]

A substance doesn’t really need to absorb the entire excess spectrum to produce a certain color as human vision cannot discern accurately between spectral colours and mixed colours. Instead, it’s more a complementary color thing where the absorption of a certain (narrow) spectrum makes you perceive the substance as the complementary color due to the absorbed spectrum being effectively subtracted from white (for the purposes of human vision at least). For green, you’d “only” need to absorb in the red spectrum just like how most green plants do. The remaining “excess” blue and yellow adds up to green.

[@pelegsap]

@@waterunderthebridge7950 good point

[@Kenionatus]

@@T3sl4 tar 🎉

[@drasiella]

You misspelled C U R S E D

[@clayton8or]

Yellow chemistry :( Geosmin :) This was a fantastic video, the subtle humorous acknowledgment of frustrations among the otherwise professional depiction made me actually physically laugh during a chemistry video, bravo.

[@Ziggyzaggy300]

"Oh wow, seems to be going good, glad he did it first tr-" "I ADDED BROMINE"

[@variouselite]

Wow. The patience. The dedication. Not to mention the skill. Mad respect brother.

[@ninjarobotmonk3y]

I love that there are smart people who are happy to share how smart they are, so I can look at all the squiggly diagrams and fancy equipment and feel like I got a tiny little bit smarter. Thanks for taking the time to create, edit, and share.

[@potumnn]

I don't know if you did an QaA about this but I was curious about the way you keep up with the things you do in your life and the passion about chemistry? Do you work as an chemist or you keep up another type of work and you make these wonderful videos on your free time? How much did you spent from the start to this day on home chemistry? When and how did you study chemistry (i imagine moreover the school education)? Did someone inspired you? Did someone has incentivated you to pursue this passion at home? Did you received or do you ask for chemistry or practical help from someone? What do your friends or parents think about your passion? Whould you ever incentivate someone to follow this beautiful path which is chemistry and sperimental home chemistry? And do you consider yourself happy? I hope you would answer these questions and remember that we're really happy to be your followers and that your's is one of the best chemistry channels here on the platform!!

[@pwaldechfal]

So sad there is no more sample, I've almost touched by the tip of my fingers one of my dreams,. This fragrance is like smelling life, its really therapeutic for me, just few breathes of it and it's like a big calm ocean with blue clear sky, take place all over my inner self. No more knots in my guts. only feather-light state instead. This a definition of a really peacefull sent. Thank you and bravo to you dear Chemiolis.

[@atescoshorse8399]

Best chemistry youtuber on the platform, love all of your videos, always excited when a new one comes out. Keep up the great work

[@julienescudero2361]

As an organic chemist I can tell you that this is some very nice work. Very impressive. Congrats!

[@tiger12506]

Like NileRed, but with a 10x harder product and difficult process. Really interesting to watch, I had never heard of that chromotographic separation process before. I don't know how the closed captions work, but there were many inconsistencies between what was said and what was in the captions. Also, I caught at least one situation where your video text said 1% HCl and you said out loud 10% HCl. This is absolutely insane, and I would have loved to to get my hands on that and smell it.... spread it around the house... lol.

[@ugarit5]

One of your best videos,outstanding reactions and an unusual compound. Very nice of giving samples of product too!

[@PepekBezlepek]

man you are an absolute legend for making this ♥ this has to be the best "amateur" orgsyn channel on youtube and I am so happy somebody is still making content like this. So many steps, great videography, narration, YELLOW memes, smell commentary. made me super happy to watch ☺ you've guaranteed a Patreon supporter as soon as I land a job. one note - audio could be louder. was hard to understand on full phone volume while showering 😆 don't judge me, that's when I got to it 😆

[@xxluggixx2559]

Pure Geosmin solutions are a part of many sensory kits! At the food company I once worked at they did taste tests of some water samples. The testers were trained by drinking highly diluted chemicals such as Geosmin or DMS.

[@I_XuMuK_I]

Oh yes, yellow chemistry at its finest.

[@edoardobandieri2688]

Your videos are always amazing, but this one is probably the best. Very well done! Keep it up :)

[@nenben8759]

I love how its cursed youtube tradition to drop a stirbar into glassware from neck height, without tilting the container

[@josepmcomajoncoses5118]

What an amazing synthesis. Congrats!! I cannot imagine the time all those steps took. Truly impressive.

[@palamalama]

Love laid back style of your commentary dude, makes this very enjoyable and approachable 😀

[@bs-qu1vq]

That was a very technical and laborious process, and you crushed it! Good job

[@RhoGamingYT]

This video is more emotional to me for some reason

[@knurlgnar24]

Of all the excellent KZbin chemistry creators including Nile Lab, Nurd Red, and Cody's Rage, Chemiolis is one of them.

[@bdnugget]

I think another good reason to add athylene glycol during the bromination is to disfavour deprotection of the ketal, since that will also yield ethylene glycol (le Chatelier principle). Oh yeah the deprotected one is probably a pretty strong lachrymator too lmao

[@lucxrio6956]

i have no idea why i watched this video the entire way through without understanding a thing. There is just something very satisfying about it. Hope it helps me in my chem final a few days from now.

[@gravity3268]

I was always told the smell of rain was from O3 (rather than the regular O2 we breathe) but I never really looked into it! Thanks for the video

[@BierBart12]

You DO smell ozone when there's a lot of static electricity, or very strongly directly after a lightning struck

[@Purin1023]

Man I love the smell of ozone. Its like spicy air

[@cyansorcerer6491]

truly an underrated channel. Watching you make this was so interesting

[@Osmone_Everony]

What always amazes me is how mother nature creates the most complex molecules with ease (apparently). Just think of all the fruit flavors for example. And here, she just let's it rain on soil and voila... Petrichor. This makes me wonder if scientists have found out how this all is achieved (especially flavors) naturally.

[@joda7697]

if we knew everything, chemistry and biology as sciences wouldn't exist anymore

[@durshurrikun150]

Fruit flavors are not that complex

[@timothydestiny3865]

Very true

[@Rich-in-Sodium]

This thumbnail is genius. Usually thumbnails are poorly made or clickbait, but this thumbnail perfectly captures the idea of the video and how we think rain SMELLS

[@SeattlePioneer]

Nature's air pollution. Probably causes global warming too, I'm guessing.

[@flamelios739]

If this guy got a dollar every time he said ‘short path vacuum distillation’, he would be a millionaire

[@Budandbee]

I always thought it was the lack of smells that made the rain smell. You learn something new every day

[@soleil_127]

i’m taking organic chemistry right now and learned the general forms of a bunch of these reactions last week ! i love it when i can start to understand what’s going on in long syntheses

[@alolfan1]

When I was 10 years old I tried to describe this smell to my class mates and they didn't understand. Thank you for vindicating my inner child.

[@mihirsanghvi9876]

And thats one heck of a long synthesis

[@env0x]

this is so cool, petrichor is my favorite smell ever and i used to have a bottle of ESO that had geosmin in it and the company that sold it ran out of business and i've never been able to find anything quite like it since.

[@chemistryofquestionablequa6252]

I LOVE the smell of petrichor! Gonna have to make it!

[@goranjosic]

I like to watch your videos when I'm tired and want to take a short nap in the armchair. I'm not a chemist, nor am I too interested in chemistry, but I enjoy listening and watching a bit of video until I fall asleep for a short time. 😃❤️ And of course Im always awake at the end to see the result!

[@PorcusCrassus]

Awesome video as always! I was wondering, though, why does the enamine form a more substituted alkene? I was always taught that it prefers to form a less substituted alkene because of sterics. Perhaps it has something to do with the fact that the nitrogen is only monoalkylated, not dialkylated? Thanks!

[@Chemiolis]

Yes that's right, normally the steric effects on a secondary amine will cause repulsion by the lone pair of the nitrogen and the methyl group, and it will favor the alkene on the less substituted position. Since this is a primary amine there is no such steric effect and it will favor the most stable position, which is the most substituted alkene.

[@etiennedauphin]

I’m an organic chemist. Well, I used to be one, I switched careers 15 years ago. Anyways, this is the first video of yours I watch. You’re pretty good. I don’t think I would’ve done one thing differently. Except I wouldn’t have smacked the column so hard (jk, every chemist’s columns are THE BEST and cleanest of the whole lab they happen to be working in). Keep it up.

[@experimental_chemistry]

So complicated that I lost track this time. 😵‍💫 It's a miracle that so much product could be obtained at all in the end. Sending smell samples was invented by labcoatz - a good idea to profitably compensate for the missing sensory impression. How about the sent of wet dog next time? 😉

[@ajax3017]

I have no clue what's happening or what he is doing but it's satisfying to see all that chemical work turn into something

[@ejkozan]

Beautiful synthesis! I really see Chemiolis perfume line a thing XD Maybe just not in carbon tet XD I understand so well yellow... yellows and oranges, most hated colours Keep good work!

[@RedHeadForester]

This man went to the ends of the earth to smell earth! I appreciate the dedication.

[@BroversXproductions]

Oh, a nice smell :). We all thought you were going to make some cursed tellurium compound or something lol

[@atakoranodonbrachiosaurus1209]

it's the best scent when one heads out- weird how one molecule (though likely a group) can bring such calm and clarity to the mind

[@raneman7415]

Can we just appreciate how mother nature just does this naturally and so quickly. Thats insane!

[@millyrocker777]

Geosmin is definitely a powerful/potent aromachemical. Props to you for having the courage to work with it in any quantity. I imagine your lab will probably smell like it for quite some time haha. However I wouldn’t really describe it as the scent of rain. If you’ve ever smelled earth while gardening or the inside of a freshly cut beetroot, thats the smell of geosmin to about 60-70% similarity. Its interesting that people liken this chemical to the scent of petrichor, when you actually smell it, its really more earth/dirt than rain/water. The watery note is there, but not very much. One day im sure we’ll find the exact composition of petrichor, and that will be my happiest day. Thanks for the video.

[@someguy8375]

I see explosions and fire is not alone in his opinions regarding yellow chemistry

[@clarkinthedark1]

That’s an extraordinary amount of patience and dedication! I couldn’t do it and would wait for the next rainstorm lol

[@SeattlePioneer]

Nature's air pollution...

[@pelegsap]

Damn, that's impressive and awesome. You deserve to get a rotovap.

[@pelegsap]

I mean, you also deserve an NMR and GCMS machines, but one step at a time ;)

[@Knot-orious]

He also deserves a cow style receiver for flasks so that he can easily change collection vessels by simply rotating into a new one.

[@idrisali8608]

my friend your videos are only getting better and better, very enjoyable

[@maqabayker]

It was not a good idea to watch this before my report deadline. Now my brain doesn't even work. Man, those were a lot of steps there lol. The videos are getting more complex day by day. I can't imagine how complex videos will be in a year from now.

[@SeattlePioneer]

Everybody needs a hobby. After listening for a while, I jumped to the end for the dramatic conclusion!

[@xerolad4086]

Ah now I get the smell referrence!

[@udittlamba]

This channel randomly came into my feed and boy, was I right to click. charming videos. you deserve to be as famous as nile red

[@Fireworker2K]

I wonder if it'd work as a perfume

[@kikoun3500]

Love you! Finally I found someone who makes videos in NileRedlike quality and fashion. Continue making videos and great content❤

[@sibazonumpurum188]

A long time a holy grail of fragrance molecules for me! But never had the balls to go all nuts and make it from scratch... Also: MgSO4 tends to "complexate" with ketoesters and diketones, which can partially explain low yields in some of the steps. I've gotten into this pitfall a few times in my practice in the lab...

[@perry4809]

Yes, make rain smell science man

[@KittenRaptor]

Processes like this are why I had to quit chemistry. This level of focused complexity and crippling ADHD do not mix. I'm writing this about halfway through the video and I already forgot what you're making. IIRC you're turning rubber gloves into McDonalds Special Sauce?

[@djillusii7333]

I always thought the rain smell was something unique to my area. Because we have creosote bushes everywhere it makes a unique rainy smell when it rains lol. People always say that rain here doesn't smell like anywhere else in a good way, so I always thought.

[@synapsomorphy]

I love your style of humor. Nothing against explosions and fire, but I can't really get into it because there's so much screen shaking and gags. You have the perfect amount of funny stuff timed just right along with 95% actual chemistry.

[@MrCh0o]

Yeah, while I'm usually up for memery, this video was refreshingly chill after watching other chemistry youtubers

[@Sinnistering]

This was an awesome video!! Thank you. I loved the chemistry, I loved the humor, just an all around perfect video.

[@KetamineKakarot]

You’re hilarious in this video

[@nimgetwereter3873]

I clicked on this video because I have some good memories from many years ago when a relaxing smell of rain would sweep through my bedroom I have no clue how you stayed awake long enough to make this video without a caffeinated IV drip I mean holy shit if I had insomnia I could just watch someone doing youtube chemistry and I'd be out cold halfway, the 603rd chemical I've never heard of would chase me on a grayscale rubix cube in my following nightmares god damn

[@DeathMetalDerf]

I really wish I had picked o-chem instead of cybersecurity...

[@MrCh0o]

How many people who were interested in chemistry but ended up choosing IT over it can we gather, I wonder

[@splash4485]

i randomly got this recommendation altough my youtube page is almost only gaming and I dont regret clicking on this! thank you for this fascinating video

[@dmmax18]

Is there a proper scientific explanation why it is always yellow and not some other goddamn color? 😅

[@Chemiolis]

I think it's because side reactions often form small conjugated systems, which are yellow because of the wavelengths these typically absorb. Since larger systems aren't formed and other colors usually require a more exotic structure, it will just make yellow :(

[@Schwello.]

Mooie video! Je wordt nog een keer een grote youtuber. Je videos zijn nu al geweldig

[@juliusbernotas]

There are perfumery channels who experimented with geosmin. There are many such materials, that need to get diluted to 1% or less in order to show their pleasant aspects. When they are pure, they just overwhelm your scent receptors.

[@jgb8038]

I'm gonna appreciate the next time it rains and I have that wonderful smell, knowing it took you so long to achieve the smell through chemistry

[@BierBart12]

Petrichor is such an unpleasant word for such a pleasant thing

[@bionicbirb9104]

also the name of the planet you play on in Risk of Rain, cool “Easter egg” by the devs

[@technoman9000]

OK, I just watched this and couldn't resist. The smell of rain is one of my favorite things so I subscribed. Hope I get a sample!

[@PonteBata]

I always wanted to make that compound. Thanks for sharing

[@IbnBahtuta]

So, it's a raining down to earth upload. Thanks, I really needed this, honest. ;-)

[@dyatlov3466]

This is not a video about chemist. This a journey through the most deep sentiment of science.

[@Forgeahead]

Three weeks ago I was looking into this. I was wanting to make dirt scented cologne. Geosmen is the main part of the smell of dirt

[@ShardHomeChem]

I wish I was able to afford this beforehand. I found an old chinese paper on this starting from the same 2-methylcyclohexanone but the whole synthesis would’ve taken way too much $. Glad to see your vid since geosmin is such a nice smell

[@CloeStump274]

Your synthesis skills are impecable 😍

[@hussaintalwara6452]

I am physics lover but now I can see my mind going in arms of chemistry.

[@dennisdecoene]

Now that my dear friend was an enormous amount of work. Well done

[@spenj]

As a newbie perfumer I only saw Geosmin used at 1% dilution. It is so strong that only a small bit could change the smell of the whole composition. But is EXPENSIVE even at 1%. Watching this feels like im on a trip.

[@perfid-deject2027]

HOLY shit...I didnt think this video would be all that cool but I always wanted someone to make this...

[@e11anora]

This is the first video I’ve ever seen from you and you’re so cool. Subscribed. Can’t wait to see your future videos!

[@KONE_OFFICIAL]

Yess a guy who uploads often, and gives damn about his channel not like nilered great!

[@crabsaresilly8317]

Ooooh yah make me lioiive bah bah bah bah!!!

[@dipankarbanerjee1130]

Chemistry lovers are legends

[@DylanoTheWizard]

hell yeah this is my type of 2 am content

[@pyroprutser4877]

I know a fellow Dutchman when I see (hear) one... goed bezig man, je hebt een kijker erbij

[@nigeljohnson9820]

There is nothing like a simple straight forward synthesis, and this is nothing like a simple straight forward synthesis.

[@Nicker000]

Love the idea of giving back to the community, supported

[@markthomas919]

Impressive stuff, take my hat off to you, amazing the process you have to go through yet after rain nature just produces it!