Which Functional Groups are the Best Smelling?
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- čas přidán 17. 06. 2022
- In this video, I JUDGE functional groups, and decide which ones smell best and worst!
/ thatchemist
Community Discord - / discord
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Links to articles discussed in this episode:
difluorobenzodioxole paper - www.doi.org/10.1021/acs.joc.0...
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Love how you seperated amines into three groups only to put all three in F tier.
Yep!
Some primary amines are uniquely bad they have names like putrascine and cadaverine for a reason
@That Chemist I had to work with amines for some time.... I always think of the garbage bin in hot summer when you put fish or prawn remains inside... Yummy! 😂
I washed my hands regularly with citric acid to get rid of that smell.
Have you ever wondered why you get slices of citron in hot water in a good restaurant when you eat shellfish? 😂
Haha, Amines are pretty terrible. I worked with Trimethylamine to make various flavours the odour is so terrible.
@@knutritter461 Citric acid - hadn't thought of that one. I used ascorbic acid -0 cause I had an 800 lb barrel of it, about half full.
Ester synthesis labs are always a fun introduction to the wide world of organic synthesis. Smells great, every reaction is a new experience, and the students learn something very important: you should always waft the smell towards you. One time we did this for a high school class, and one kid placed his nostril over a test tube and took a deep breath of a propanoate ester. He said it felt like a pineapple punched him in the nose.
Oh no haha
Ah. I have been that kid once. Never again
Now i really want to try it
Ester practicals are a highlight of 16+ courses. The butyrates however are forbidden fruit as most of us do not want butyric acid smells in our labs. Just about thole propionate. Benzoates rule.
Methyl Salicate is one I always make sure gets made - a very familiar smell in schools. (That one not S tier!)
For those who aren't familiar with chemicals and chemisty, please do NOT huff these or any chemicals. always waft the vapors with your hand up towards your nose.
Sometimes it's a fast-track ticket to the floor.
Especially with ethers or chloromethanes
We once had a lab where we had multiple beakers at the end, some were organic some were halogenated and no one had labelled their waste, so the lab techs had to go around the fume hoods smelling every beaker to determine which waste it went in
My colleague almost screwed himself with ammonium nitrate (aq) this way
yeah, don’t be a chem sniffer
in a synthesis exercise i got to smell 2-methylpentanal, which had a strong nutty smell. i think it was nice, but surprising how it overpowered the diethyl ether it was dissolved in. the product was 4-methylheptan-3-ol which i described in my notes as "cut grass vegetable mint soup-tea". had to sniff it for a while to find the right words.
Interesting!
Homestuck
homestuck
@@friedchickenUSA I really don't need to be, homestuck has already ruined my life
I feel that the smell of a lot of compounds depends entirely on the concentration (?), someone was making some organoselenium compound in the hood next to mine, it first smelled like baked beans, then after a while it smelled like moldy meat, then it smelled like death
Yeah that’s a valid point
Isn’t there also a decomposition/faeces compound (I think skatole) that smells like flowers and nice things in very low concentrations but turns to literal sh*t and death at higher concentration
You got a point but I think the tierlist should be based on the smallest concentrations (just wiffs)
Mostly because you dont wanna be taking breaths of ethers or those scary fluorine/sulphur compounds
Similar with organosulfur compounds. I went from "who brought onions" over "Jesus what did you eat to let out this fart" to "OH SHIT GAS LEAK"
True. The thresholds also change from person to person. For me, geraniol becomes unpleasant much sooner than it does for the average person which means that many "flowery" perfumes and shampoos smell like the unpleasant "green-ness" of geraniums to me.
A mine I used to work in used methyl mercaptan as part of their emergency alert system. When there was a situation that required everyone to report into the refuge chambers underground, a 10lb bottle of this stuff was dumped into the fresh air supply for the mine. I felt sorry for the person who had to release it.
Oh my gosh, that’s brilliant
A mercaptan plant blew up once near Paris. The gas company in Southern England was inundated with reports of leaks.
Cold benzaldehyde is like the best smelling compound ever. Key word COLD. I remember my first dibenzylideneacetone synthesis. I didn't use an alcohol to dissolve the benzaldehyde, and it was on excess, so the product dissolved in it. I had to boil it off to recover the product. It basically smelled like rotting, burned, old and potentially toxic cherries. Or if someone took a shit into cherry compot.
good for animalic cherry fragrances lol xD
I was trying to synthesize benzaldehyde and counted on fact, that people consider it very nice cherry smelling. Well... It's not really at least when not cold and concentrated... it almost smells like chloro toluene with slight cherry undertone. Really awful...
“Burning fruity skunks” has to be the best and most accurate description of a fragrance ever.
17:57 I totally agree, solid 100% for F-tier also from me. I almost threw up when I worked with cyclopentyl mercaptan which reminded me of rotten onion + chives but surprisingly cyclohexyl mercaptan reminded me of cat urine (just change of -CH2- group). Someone in comments mentioned about concentration - they're absolutely right, benzyl mercaptan in very small concentrations smell like morning coffee, then turns into garlic to finish as burned rubber. I remember, once after work I entered my dad's car and he immediately started panicking because he thought something was burning in the car.
There is one unusual exception - although thiophenol reeks, thionaphthol smells like forest edible mushrooms. Maybe it depends on individual perception?
Yeah benzyl mercaptan is a perfect example
Yes cyclohexyl mercaptan smells definitely like cat urine
I have my personal fragrance research going on for a while and have a small collection of aroma chemicals. Personally I think while functional groups do matter a lot, the overall structure, shape, and specific features (like the distance between certain functional groups) are also very important contributors to the odor of a compound.
For example, spherical or nearly spherical molecules (or parts of molecules) tend to smell camphoraceous or maybe a bit minty regardless of functional groups. This is probably why tert-butyl or cyclohexyl compounds tend to have such smell though they aren't technically 'functional' groups. I once worked with p-carborane which is an eicosahedral molecule C2H12B10 or (CH)2(BH)10 and was surprised by its scent - strikingly similar to camphor! Also, just think of the wide variety of musky-smelling compounds. Nitroarenes can smell musky (e.g. musk ketone, musk xylene) - the first artificial musks were discovered accidentally in an attempt to make explosives. Polycyclic musks are the most widely used today and they are typically benzo-fused (oxa)cyclopentane/cyclohexane derivatives. And natural musks are usually macrocyclic ketones. My all-time favorite smell is muscenone - such an elegant, sensual, sophisticated, and sweet scent! It can even have floral and woody undertones.
Also concentrations matter. While thiols are bad at 'normal' concentrations, trace amounts contribute to the 'natural-ness' of many fruits, vegetables, meats, rosted/baked foods, and even roses! Aliphatic aldehydes while pungent at high concentrations, are important in trace amounts in so-called 'aldehydic' notes in perfumery. Some say they make the floral scents sparkle and some say they make perfumes more 'intimate' or 'sensual' smelling like a real person's skin or hair with some sebum on it. But overdosing them does make that old-person or metallic smell. The same goes for nitriles - people say they typically smell like their aldehyde counterparts but sharper and a bit more metallic. Trace amounts of nitriles are good as aldehyde substitutes in fragrances especially for functional products like detergents due to their greater stability.
Back to functional groups - if I have to rank the best smelling functional groups, I'd have lactones separate from esters. If esters are S tier lactones are definitely S++. Gamma-decalactone, undecalactone, and dodecalactone are the soft, fuzzy, and powdery part of peaches. And interestingly enough, according to several Japanese studies, the former two contribute significantly to the natural body scent of young women of 10-30 age. Delta lactones just remind me of tropical paradise - coconuts, fruit cocktails and suntan lotions. Delta-jasmolactone is wonderfully soft, creamy and floral at the same time. And it's hard to forget how good those macrocycic lactones smell like once you take a first whiff of ambrettolide.
Wow, I wish I could smell all of these!
Amazing! Are there commercial fragrances that you would recommend for experiencing lactones?
Tributyl phosphite has a skunky odor. Back in the 1970s I was cleaning out a fume hood with a bottle of tributyl phosphite. The bottle was covered with a slime so when I picked it up it slipped out of my hand and fell onto the floor and broke. I then mopped up the spill and put that mess into a sink. Unbeknownst to me all the sinks in Bagley Hall (chemistry building) on the University of Washington were connected to a single trap. So I succeeded in stinking up the entire building leading to an unorganized evacuation of the building. Tributyl phosphite per the poison control center is not significantly toxic. Its only effect is to make anyone who comes in contact with it to stink. Any mild oxidizer will get rid of the stink.
That sucks so much
Someone in the lab worked with phenylacetaldehyde and it was the weirdest thing because I would walk past one part of the lab and be like "flowers? in the lab?" and that lasted for about a week until the smell dissipated.
It’s controversial
Phenylacetaldehyde has a very powerful smell and trace amounts of it are responsible for the heady green top-note of many flowers. However it is rather unstable toward long-term storage especially in alcohol-based perfumes (forms acetals readily) or acidic/basic media (polymerizes). Therefore the fragrance / flavor industry usually uses its pre-formed acetals like PADMA to get more stable and reproducible effects.
@@YuPuWang That's cool, I'm interested to learn more about perfume/fragrance chemistry. I just love smelling chemicals.
@@YuPuWang You should become a content creator.
I’m surprised pyridine didn’t get its own mention, it will always be my least favourite chemical, it’s truly disgusting.
I hate the smell of pyridines
Pyridine does worth its own place. For me it is like sewer with putrefied dead fish and frogs in it.
However, certain alkyl-substituted pyridines - in small concentrations - in addition to being useful as food flavoring, can also add realism to certain types of fragrance notes (e.g. green, aquatic, and gourmand).
🤢
Yeah APHP smells like semen, really gross
@@That_ChemistI haven’t really smelled them, but from this description... easy peasy F tier.
you're the best smelling functional group in my opinion, joey 😍
Smh
I can smell your profile picture sir
Ester Synthesis was one of our labs in Engineering Chemistry (which is GenChem and OChem crammed into one year) and it was by far the best the lab smelled that year.
awe yiss
sina toki e toki pona anu seme?
@@owenyoshida9202 what makes you think that?
Diphenylether has a very potent smell (it is used as a substitute for ambergris in perfume bases) that is somewhere between very unpleasant and suffocating. A production plant where I worked in an earlier job blew a rupture disk one cold January day in Michigan and it actually was snowing diphenylether over the plant site. Our building didn't shut down the air handlers fast enough and most of that day was spent trying not to vomit.
hahaha that's amazing
I've worked with diphenyl ether (as a high-temp solvent) a couple of times. To me it smells like the sharpest greenness of geraniums. Not necessarily a bad smell in low concentrations, though.
Definitely agree with alcohols. I prepared a couple of kilos of 3-trifluoromethyl cyclohexanol by hydrogenation of the phenol, it was one of the nicest smelling reactions I've ever done. I made phenylethanol isomers while trialling a Rh catalyst in the hydroboration of styrenes and they definitely smell incredible.
Acetophenones are also amazing, 4-fluoroacetophenone smells strongly of bakewell tart to the point that spilling ~1 ml of it in my PhD hood made my lab smell of it for the morning.
One final comment, butyric acid is the smell of vomit and rotting dairy products. My lab partner in A-level chem spilled it on my ungloved hand, and that hand smelled of puke for a couple of days.
That’s awesome - I always forget that you can hydrogenate arenes to make cool Cyclohexane derivatives
I don't think it really counts as "working" with chemicals, but I absolutely love the smell of allicin and syn-propanethial-s-oxide from "working with" (aka chopping and eating) onions, garlic, and chives. Easy S-tier for me, since they smell delicious and it has an S for sulfur, one of my favourite elements.
I'd rate ethers higher. Havent smelles tons of them but diethyl ether is generally a enjoyable smell for me and dibuthylether has a nice pineapple smell
I'm willing to fist fight you! I don't understand why people love ethers. One of my lab colleagues also swears by diethyl ether, saying it smells nice. To me, it smells bad! I'd take acetone, ethanol, isopropanol etc any day of the week over diethyl ether
To me it has that sharp sting in the nose and the overall "bouquet" is just not enjoable. Couple that with the fact it's so volatile you always smell a lot of it if you're near, it's bad. Not bad like amines or sulfur compounds, but it has nothing even on simple alcohols
E: speaking of sulfur compounds, I'd go so far as to say that hydrogen sulfide smells better than ether. Of course I'd never inhale large concentrations of it because I don't particularly want to inhale a gas as toxic as hydrogen cyanide, at this point in life anyway, but in dilute concentrations it's much less offensive than ether
Im currently working with azides, and its really a wheel of fortune smelling game
In one hand, I have sodium azide, which (in addition of being dangerous) smells absolutly horrible.
In the other hand, I have tetrabutylammonium azide which is a no-odor white powder. Some coworkers said it smells like old books
Wait why are you actively smelling Sodium azide... Sodium azide shouldn't have a smell, you're smelling Hydrazoic acid
@@ChoumadaGaming yeah its hydrazoic acid, but I linked it too much with sodium azide to make a distinction as this point
funny thing is that i use sodium azide to make tetrabutylammonium azide in aqueous conditions, and even with 10 equivalents, no smell whatsoever.
Some guy in my undergrad lab project, tried drying (yes drying) ether in the glass drying oven. We found it in time luckily, but safe to say I now hate the smell of ether and I’ve never had a more annoying headache ever. It’s just so intense. So many stories about the same guy
Haha
Someone who does one dumb thing often does many dumb things
@@00bean00 diethyl ether does form a hydroperoxide when exposed to UV light, but I’m pretty sure suppliers put stabilisers in to prevent it from happening. I’m sure an increase in temp will speed that up tho.
However, the issue was more it was boiling in the oven as it’s boiling point is about ~34°C, and it was just filling the lab which is really dangerous. Also potentially auto igniting is not a pleasant thought.
About 20 years ago in O Chem we had to extract eugenol from cloves. A drop of it fell on my lab notebook and the smell lasted a surprisingly long time. I love it though.
My Biochem prof once shared that when she was in university, someone had dropped I think butyric acid in the vents and the smell stuck to her all day, and had to take public transit to get back home at the end of the day. It was uncomfortable, to say the least.
I actually hate the smell of cloves - it lasts seemingly forever!
I remember making esters for the first time a couple months ago. I think it was propyl propanoate I can’t really remember. My friend and I just kept smelling the stuff, it smell like pears but somehow even better, hope there wasn’t any left over sulphuric acid. Funny thing is that a few minutes before I wanted to leave the room because of the smell of the propanoic acid, how can two things that smell so bad make something that smells so good.
Thioacetone is a very mysterious compound for me somehow.
I read story’s about just a little bit of it being sucked outside through a fumehood, and ppl 500m away starting vomiting because of the smell.
Hard to imagine for me that a stench can be that potent.
Strangely there is more than one story from ppl who smelled it.
Can u maybe tell me more information about Thioacetone smell ? Can it be compared with something ? Is it really that awful even in small quantities?
For me it has a “u can’t make it without having someone calling the fire department” character.
Would be great to hear some more first hand descriptions.
Smell is hard to transmitting over CZcams 😅
To me, phenol just smells like old circuit boards, mostly because they contain polymers made with phenol.
1-Naphthol is also... not awful but it's incredibly strong and a bit irritating. I got some on my skin once and could smell it for days, even after multple thorough washings and showerings.
Wow that is sketchy
@@That_Chemist Not as sketchy as my (probably failed) attempt at making isocyanides in the lab. I smelled nothing and no one complained about any smell
Phenols smell like smoke to me.
@@martinofgliwice1486 Probably because Islay malt whiskies mix peat smoke with phenol.
@@1mctous I never drank whiskey. it is not popular here where I live.
Great video as always! I've done a decent amount of making perfumes and I'd agree there is no place for those compounds you were talking about. I've used lots of esters, benzyl alcohols, aldehydes, longer chain alcohols, allyl compounds, and surprisingly quite a few indole derivatives but those have to be very dilute. They smell very musty and like animals in a bad way above 1-2%, below that they smell very rich and complex
Interesting!
I would love to see you formulate a perfume collection with this knowledge and show the process!
lavor chemists are in high demand, along about end of 2022. Just Sayin.
Heyy! Great video as always!
I personally have a soft spot for esters, so this topic is really intriguing for me. For the functional groups I know, I'm with your ranking almost always. Maybe great minds do think alike. Have a great one TC! 😎
Thanks :)
I agree benzaldehydes smell good.....well except one I know of. Salicylaldehyde. Just made it and its not exactly what I expected so much so I bought a sample for reference and its the same smell. Phenolic and reminds me slightly of Benzyl alcohol and also the strength of that smell turns me off from it. 2-phenylethanol is really nice when diluted some. I made a scentsy cube or whatever theyre called but i used phenylethanol and helional(i thought helional was going to be a flavoring since i bought it from my flavoring supplier but the bottle said sold for fragrance purposes). I like to use it as it makes me place smell like rosey and fresh like an ocean breeze. You definitely brought some new to me smells that im curious of now though. Great video dude! Always love them!
interesting!
I have a small collection of aroma compounds. I really enjoy the smell of fructone, which reminds me of pineapple. Also really like the smell of methyl cinnamate, nerolin and acetanisole. This last one my mom didnt enjoy. Need to get myself some benzaldehyde, anisyl acetate and helional.
My favourite smelling chemical i've made is 1-Deoxymannojirimycin (Imino-sugar) which the freebase has a nice nutty/woody smell. Would make a great cologne i think
I remember using various phenolic bromides for a synthesis project with varying degrees of ether-ification. All very interesting smells, good and bad but mostly smokey
As someone who hasn't worked with phosphines but have been in the lab while others have worked with them - I'd put them in F tier.. there's one specific phosphine ligand that triggers migraines for me. It was worse than then getting HCl gas in the eyes. TsCl is a solid D tier imo.. My definitive ranking there lol
For me, aryl phosphines are fine, it was the alkyl ones that really reek. Especially the small, volatile alkyl phosphines are literally amines on crack. According to S. L. Buchwald, trimethylphosphine is like you take some fish out of your freezer to thaw on the cutting board, and while it is ready to be cooked you got a phone call from friends to help them move. You only return home a week later and open the door, suddenly realizing there's fish from a week ago and it's the middle of August...
2:00 nilered released a video of him making thioacetone back in january or February. He said up close it didnt have a significant smell (the cameraman disagreed) but the farther away he got, the stronger the odor was.
Teachers:
Dont smell anything in the lab, everything should be in a fume hood!
That Chemist:
Haha, chemical smell tier list go brrr!
the smell test would be awesome, looking forward to that possibly happening
One of my recent organic labs involved getting an unknown carboxylic acid and an unknown alcohol to perform the Fischer esterification. We then had to identify the ester using H-NMR. Turns out I had synthesized benzyl propionate, which has a lovely apple/jasmine smell.
One group I was kinda expecting was non-aromatic cyclic alkenes. Cyclohexene and cyclopentadiene are classic intense, penetrating, unpleasant smells afterall.
A chemical that really surprised me was 2-amino-thiophenol (or 2-mercapto-aniline, same difference). I expected it to smell absolutely awful, but instead it just... smelled like... idk, a greasy rotissery chicken? With only maybe a faint hint of toilet? Smells are hard to describe :Y
Haha - chicken toilet is a smell I can’t say that I’ve smelled - I’ve worked with 2-aminophenol, but I don’t recall it’s smell
Benzaldehyde S Tier is is relatable. Once during my time in vocational school we did a synthesis with benzaldehyde, afterwards the entire class wanted to go drink some almond liquor afterwards (yes, we were all above legal drinking age, 18 in my country). Was quite a funny day.
Understandable
Two chemicals I've worked with come to mind that combine what you discussed quite well: methoxyethyl acetate and ethoxyethyl acetate. By and large they smell pleasant (likely the ester group), but there was always a hint of something off, like a stutter (probably the ether). In a word, they are "p-pleasant".
Interesting
Aww man, I remember doing alcohol to aldehyde reactions in my chemistry A-Level and I have to say acetaldehyde is one of my favourite smells... it has a smell that nothing else smells like!!! Might have been propanal as well as we used to do ketone reactions too, which needs a secondary alcohol so I assume we also converted a primary propanol!
As a chemist working with SF4 for deoxofluorination, I must say that CF3-derivatives often have a pleasant odor. Easy A-tier
True
in 1978 I was working with Joel X ray fluorescence spectrometer. Its high voltage transformer was in a box with oil. I was told not to open it, but being in my 20s, I tried to smell it but almost knocked me over. Felt sick for hours. I don't know what it was but to this date was the worst smelling organic liquid.
Thing is with diethyl ether is you keep on smelling and it pushes right back into smelling great again!
I want to comment here to say I am an aspiring biochemist and seeing your content here is inspiring! You are putting out such an incredible volume of great quality materials that it is truly impressive!! Keep up the great work!
Thank you :)
I *love* phenols. Related (and missing from your video), Toluene. Absolutely gorgeous. Probably shouldn't breathe it in, but still nice.
True
Story time: the first time I had to work with Mercaptan.
As part of a QC job i had I was required to do some regular raw material testing for a flavour lab. That day their lab manager I reported to was with a client so I just grabbed the first work off the top of the todo pile.
The sample, already sampled for me awaited in the storage fridge... Around 5ml of a oily clear liquid within a sealed glass vial in plastic bag within a plastic box. Huh seems overkill but oh well I thought.
Now I was no stranger to the potency of some of the compounds so I wasn't going to just open the vial on the open bench - for example I previously had to do work on butyric acid (the smell of baby vomit).
Taking the sample to our lab upstairs I prepared our FTIR spectrometer within a fumehood (as part of the test I was required to compare the sample spectra to compare to reference spectra).
Now here is where the mistake was made... I opened the container to take the sealed vial out on an open bench and left the box open as I took the SEALED vial into the fume hood. However, the compound in question was so potent that just the inside of the box smelled horrifying.
Completely obliviously I started testing while people started complaining of a strong gas smell. By the time I had competed testing enough panic has raised that the safety officer was in the lab asking people to leave because of reports of a gas leak.
Turns out I had become so desensitised to the stench while working didn't notice the similarity to gas at lower a potency. (to me it just stunk of dog poop?)
It was quite embarrassing explaining to people for the rest of the day that the building was safe and it was just me working with thiols.
Awesome
@@That_Chemist not how I would describe that situation but I'm glad you enjoyed the story! 🤣
One of the most pleasant smelling chemicals I've smelled is methyl benzoate. Of course aryl alehydes. Although cinnamaldehyde smells like spit or funky body odors in very high concentrations. But diluted in small amounts, especially with a little vanilla smells awesome. One of the worst was either tritheyl phosphite or pyridine.
Fun fact - they train drug-sniffing dogs to smell methyl benzoate as an indicator for the presence of cocaine
@@That_Chemist That methyl benzoate probably comes from self-transesterification of cocaine as it contains both methyl ester and benzoate ester.
One of my sleeper favorites is alpha terpineol, though it’s hard to describe. The worst I’ve worked with were adjacent dithiol. Dithiols/dimercaptans in general are bad. 1,4 dithiols smell like skunk and are closely related to actual skunk musk.
I love the smell of TBDMS-groups so much, and how cool is it that you can tell whether your protection worked by smell?
well it would be cool, but you could just have TBS-OH and ROH
OMG yes, do a video of a bunch of ppl smelling compounds ♥ similar to Tom's salt testing vid :D
In my 1st year lab I synthesised ester which smelled really nice, just like peach... but I smelled it before evaporating dcm, so ended up being kinda high for some time
sounds pleasant :)
21:46 I don't know if it was related to allyl groups, but my mother had an almost allergy-type reaction to onions and garlic. She found the smell of both to be quite noxious, and if she actually consumed them, she would get feeling quite sick. It didn't help things that she married a half-Italian man.
in the lab I work with 3-mercaptopropionic acid and holy hell it smells so weird and unpleasant. it's as if it strived so hard to smell like popcorn only to fall down a huge flight of stairs, breaking all of its bones in the process and becoming bedridden for the rest of its life. also its smell has an annoying habit of sticking onto anything it touches and lingering there for weeks and even months on end despite any concentrated cleaning efforts. sad stuff.
Eww
Diluted iPrOH actually smells really good. I had an impromptu experiment involving a leaky spray bottle filled with 91% iPrOH and a hot car, and it had this really peculiar, earthy but delicious smell. Delicious in that way that some lip balms are where you know it won't actually taste good but your brain says eat it. That burning, antiseptic harsh smell is only really noticeable at high concentrations imo.
yeah I agree
Also I do use isopropanol extensively and tbh I only avoid breathing it in because of metabolites, the smell is pretty nice, perfume like :D
of course esters are at the top, we all know that "S-tier" got its name from someone mispronouncing "ester"
Haha
Tosyl chloride doesnt bother me. I kind like a lot of the "bad " smelling sulphur compounds anyways. Surpricing variety of aromas in those too outside generic surphury smells.
could not agree more about tosyl chloride. Propargyl thioacetate was definitely the worst smelling thing I've made, although I was really shocked by 1-pentyne. thiophenol smells like bacon at really low concentrations strangely enough...
I always find Methyl Ethyl Ketone smells somewhat like Acetone, but just a bit different. Like Acetons cousin!
it has some other vibe going on - its like acetone's hot cousin
Acetone with a bit of butterscotch. I kind of like it, in moderation. Like a hot cousin.
I think Methanol smells great, it reminds me of my school days.
Its the smell of fresh mimeograph copies, everyone huffed them as soon as the teachers handed them out because the smell
Man, it seems like some chemists have way more breadth of distinct smells and attributable significance to them than most people. My nose mostly tells me when something is hot or burning. It does that job very sensitively and with some differentiation but almost totally ignores other scents.
@@00bean00 Not to my knowledge, and I'm significantly more sensitive than most people in that limited palette
15:00 Amines tend to smell nasty but some smell nice. Methyl anthranilate smells like flower and grapes.
16:25 If you like cyclohexanes, then you must smell helvetolide and edenolide!
18:00 thiols smell nasty but in traces are important in some flavors, and grapefruit mercaptan smells like grapefruit.
25:30 secondary amides smell nasty but can also smell good. Paradisaide smells fruity.
27:00 Ketones can smell harsh or smell great. Rose ketones smell amazing.
I will look into this :)
I will never forget smelling part 2 of old decomposed Marine-Tex epoxy. Methylamine times 100 supposedly the compound is 'Polyamines'. Penetrating toxic evil death fumes, sooo bad.
I always wondered what aldehydes smell like because some perfumes just put "aldehydes" as one of the notes.
What does the Y attached to the cyclohexane and chicken feet stand for? Like it can't be yttrium right?
Some group, usually indicating another element besides carbon
I’m totally not a chemist so I don’t know what it’s like, but it surprises me that you smell all the chemicals you make. I would think that it’s too risky or bad practice
usually its inevitable that you smell them - I'm not going HAM and shoving the chemical up my nose, I just gently waft the smell towards my nose
It seems weird, but an accepted operational mode in organic chem labs to have enough of something in the air that you can smell it while working with it. Just transferring between fume hoods or whatever. That's generally a very low concentration, and if it was dangerous at that low concentration it would be pretty special and special precautions would be taken, or more likely no one would be interested in doing that kind of chemistry, for example nerve agents, one whiff dead. (odourless regardless).
I stumbled upon a bunch of silyl ethers that smelled like petrichor but better. I miss them.
I got to work with the bromine analog of mace and it just smelled like cherries/red hots to me, vaguely spicy but mostly fruity, I wasn't sticking my nose in it though so maybe it's not a fair assessment
Mixed organic solvents (essence of solvent cabinet): S+ fight me cowards
Onee rather simple ester smells like superglue. I don't know if I would describe that specific one as S-tier, but most others definitely are.
volatile compounds with SeH and SeR groups from locoweed plants smelled like gunpowder so not horrible like thiols and mercaptans but not pleasant either
When using mesityl bromide, my syringe broke and I got it leaked all over my hand. I expected it to smell stingy or like cancer, but instead it had a very strong lemon smell which took so much soap to get off.
Interesting! It’s probably still pretty toxic imo
Small carboxylic acids, like vinegar and formic are interesting but the bigger ones are pretty gross. Phenol itself makes me think “clean”, like antiseptic, but also that it just wiped out the lives of all those little bacteria critters, poor dudes :(
I also wanted to make the point that acetic acid is quite ok to smell (in small amounts). Phenol is actually contained in certain whiskeys (like Laphroig) and some people love it while some people hate it.
I’ve never smelled any of these, not that I know of/am aware of/remember. Two questions:
1. Would methyl salicylate (wintergreen flavoring, my personal favorite, smell-wise) fall in any of these categories?
2. I’ve seen a few comments praising benzaldehyde. What does it smell like?
Methyl salicylate is great - it is both a methyl benzoate as well as a phenol - it is nice but it can be toxic in high enough doses. 2. Benzaldehyde is the typical almond/cherry flavour
A former colleague once made 1,3,5-norcaratriene (basically benzene with a cyclopropane fused to it). That stuff smells awful down to very low concentrations and I have no clue why.
weird!
If you are of a certain age and lived in Somerset, you will know the Bridgwater smell. Came from the British Cellophane factory which like most British factories is no longer there. A bit Carbon disulphideish, I have no idea what it was but it is unforgettable. Fortunately encountered nothing like in the lab. Travelled miles - F Tier!
Chicken feet and difluoromethoxy groups are S+.
Thiols, sulfides, selenols, selenides, amines of all kinds, carboxylic acids and their mono- and dithio derivatives, and mono- and dithiocarboxylate esters are F, however.
chem noob here, what’s the difference between R, R’, and Ar? im guessing Ar isn’t argon since it doesn’t tend to react much, and my guess for R and R prime is mirrored versions or stuff that’s completely different, but i have no clue what the difference between R/R’ and Ar is. also Y.
R and R' just means "some thing, usually a carbon" and R' just means it can be a different thing than R is - Ar means aryl, and it just means some benzene ring with various substituents
@@That_Chemist cool, thanks for the explanation
I share your dislike of diacetyl. Certain British ales (Bass) contain some diacetyl from fermentation by-products and I tend to avoid them. I also make my own popcorn from kernels and oil for the same reason.
in my orgo lab we used methyl benzoate all the time... a ton of people liked the smell but for me it always gave me a headache and made me want to puke. it's pretty volatile so I'd just spent the entire session like 🤢 lmaooo
“Burning fruity skunks” - there’s a unique description!
I used the 1,2ethanedithiol (EDT) in a cleavage of peptide form the resin and I got in a real problem for the smell of rotten eggs and drain smell it didnt last long (like 5 min) the smell but it was really strong XD
Personally I love smell of acrylates, MEKP also has very nice ozone-y smell to it
I hate acrylates with a passion
I cannot imagine anyone liking ethyl acrylate, which is just horrendous. Methyl acrylate is not as bad, but more toxic. I like n-butyl acrylate though.
I really like your work! I don’t think I’m capable of achieving a true understanding of organic chemistry. I do however work in a wastewater treatment facility; I was kind of willing you to hit Urea earlier on.
Objection to certain compounds I think will always be subjective. I’m completely on your side when you euclidiated that there are certain compounds that smell cancerous or dangerous. I’m sure you have a fume hood in the same capacity that we use SCBA and decontamination procedures.
I am subscribed! I am also ultimately a layman and absolutely appreciate your work.
Okay but what if you had C6H4COHCSCH3. Does the benzaldehyde make up for the thioketone?
Presumably the thioanisole wouldn’t have much impact on the smell of the benzaldehyde
@@That_Chemist im aware that you can't really just stick chemicals together and there's probably some clever reason why that can't exist. Still though, fun to think about massive molecules with dozens of functional groups that behave opposite to each other.
"...smell like burning, fruity skunks..." "...garbage or unclean bottom..." 😟... 🤣🤣🤣
Thanks for making me laugh so hard, all the way through the video!
I kinda disagree with Aldehydes being in the D Tier, but only from a Perfume standpoint. In Lab they might really smell pleasant and/or meh, but in Perfumery Aldehydes are very common in use and even made Channel No.5 so crazy famous, the Aldehyde 2-Methylundecanal, I would love to see a Video of you reviewing Perfumery Chems.
yeah but chanel no 5 literally smells like an old person
Let me recommend "Common Fragrance and Flavor Materials: by Bauer, Garbe, and Surburg. (Wiley)
Your voice and delivery makes me think Casually Explained has been secretly studying chemistry!
Haha
If you have alcohols in A tier you’ve never smelled fusel oil (mix of butanols/pentanols) that stuff is FOUL
I would bring phenols up from D to B, its not any kind of natural good smelling but for a chemical smell its pretty nice.
I see your ethers in D and raise you vinylethers. They smell like the essence of glue to me and i love it xD
vinyl ethers smell bad
Real talk, I keep a little bottle of acetone around to sniff sometimes, smells so good
I really cannot understand how people like the smell of acetone.😂
Haha
Acetone is some kind of pleasant for me, when smelled in small concentrations.
I would personally favor toluene or just gasoline for cars 😄
Or try things like isopropyl nitrile 😉 sometimes they sell it in small handy bottles 😄
However it is probably not the best habit to keep bottles of chemicals around only for smelling them😂
I definitely love the smell of ethers, and how dare you say that isopropanol and ethanol smell bad! (I definitely never played around with isopronal/dry ice for hours)
What job would anyone have where they are synthesizing this many different compounds? I got a degree in chemistry and the only jobs I was ever offered in chemistry were at Chevron and cannabis companies. Needless to say I’m a software engineer now.
organic chemist in method development
@@That_Chemist that's the sort of job I would have wanted.
I was obsessed with organic chemistry from high school all the way until I couldn't find a job after college. All my young adult life I was sure I would become an organic chemist researching medicine. After I got my degree I couldn't even find someone who would let me volunteer my time. Not even soil labs would hire me.
I ended up working as a microbiology technician at Genentech, turning the same 20 valves for 12 hours a day. I tried to interview there as a research assistant and they told me to come back with a PhD. I was told that the only way up the ladder was to leave the company and come back in through a different door; that technicians stay technicians.
I never wanted a PhD. I wanted to be in a lab working, gathering data, coming up with ideas. I would have lived in the lab if I could.
The only chemistry I do now is when I de-lime my toilet bowl. I feel like part of me is missing.
I used to prepare ~100ml batches of Ar-N+≡C- via the :CCl2 process, splashing the product here and there, then having fun watching the horrified passers-by :). IT'S A TRAP!!! Nope, 't'ain't a trap, 'tis intentional :).
"it smells like onions, but something is wrong" what 💀💀
Acetonitrile smells good to me, sweet and fruity, reminescent of cherry with a distinct chemical but inoffensive note. Favourite smell as far as the molecules this small are concerned. But I am not too experienced.
Interesting!
I agree
Next episode... The forbidden tier list - Best tasting chemicals
Maybe someday ;)