Sciencemadness Discussion Board

What was your first organic chem experiment?

NEMO-Chemistry - 10-10-2017 at 03:34

I am curious to know what experiments people did as a first organic chem lab.

Organic chemistry seems to be a real sticking point with me, but i learn best by doing, however reading books on it and trying those experiments, ends up costing me money and ending in failure..

so different approach, ask what people normally do as a first experiment, then research that and start from there. End goal for me...........

Developing testing kits for edible mushrooms that are slightly exotic. no not the trippy ones, but the extremely expensive posh restaurant ones :D

LearnedAmateur - 10-10-2017 at 03:45

In school we mainly did esterification reactions for organic chemistry because they're quite simple and show how to manipulate reversible reactions. One notable one we did was the synthesis of aspirin using salicylic acid and acetic anhydride, and also the synthesis of methyl salicylate then subsequent hydrolysis. Other than that we did a few alcohol oxidation reactions although this was mainly centred around the colour change associated with dichromate, and various tests such as Tollens', DNPH derivatives for melting points, and the hydrolysis of haloalkanes to observe their relative rates of reaction. At home I've done some extractions of plant matter, a great way to learn about the properties of solvents and salts, oxidation of toluene to benzoic acid, aryl sulfonation, and I've made some alkyl nitrites as well. These are all fairly basic and are neat intros to the topic, and if you're worried about costs and failure, you don't have to play around with more than a few grams at a time plus it's quicker, and easier to tweak, observe, and control. Hope that helps a bit

NEMO-Chemistry - 10-10-2017 at 03:55

Quote: Originally posted by LearnedAmateur  
In school we mainly did esterification reactions for organic chemistry because they're quite simple and show how to manipulate reversible reactions. One notable one we did was the synthesis of aspirin using salicylic acid and acetic anhydride, and also the synthesis of methyl salicylate then subsequent hydrolysis. Other than that we did a few alcohol oxidation reactions although this was mainly centred around the colour change associated with dichromate, and various tests such as Tollens', DNPH derivatives for melting points, and the hydrolysis of haloalkanes to observe their relative rates of reaction. At home I've done some extractions of plant matter, a great way to learn about the properties of solvents and salts, oxidation of toluene to benzoic acid, aryl sulfonation, and I've made some alkyl nitrites as well. These are all fairly basic and are neat intros to the topic, and if you're worried about costs and failure, you don't have to play around with more than a few grams at a time plus it's quicker, and easier to tweak, observe, and control. Hope that helps a bit


That helps alot

i already do alot of plant extractions, its kind of my main interest because i make natural soaps.

Not sure i can get acetic anhydride, i will have to check. i am in UK and lately alot of stuff that was easy to buy 6 months ago is getting really hard. ADD sulphuric acid to that!!

esterification reactions look a good fit, as long as i can get/make the reagents. Thx anyway, you have given me a good list to research and get started.

I did a year of non organic chemistry, because i got low grades in the exam (i missed first two months of the course), i wasnt allowed to do Organic chem.

DraconicAcid - 10-10-2017 at 06:59

I'll chime in here, too- when I taught first-year organic chem, we started with recrystallizations and extractions (including separation of acids or bases from mixtures by extraction with aqueous acid/base, followed by neutralization, and extraction of either caffeine from tea, lactose from powdered milk, or piperine from pepper). Chromatography of spinach extract to get chlorophyll and carotenes.

Oxidation of alcohols using bleach and acetic acid (this only works if the oxidation product is sufficiently hydrophobic to be extracted with organic solvent), esterification (god, I'm tired of the smell of isoamyl acetate). We also did Diels-Alder of some sort, we reduced vanillin to the alcohol, various electrophilic additions to aromatic rings (some classes did bromination, some did nitration, and others did Friedels-Craft acylation).

NEMO-Chemistry - 10-10-2017 at 07:11

So turns out I have already done alot of the very basic stuff without knowing it. That makes me feel better at least.

so by DA's list I am at caffeine extraction (done chromatography alot). Lactose looks interesting so will do that at the weekend. piperine i would do but seems i have a bit of an allergy to pepper.

At some point I want to do a Wacker reaction simply because i am childish and love the name.

NEMO-Chemistry - 10-10-2017 at 07:27

Incase anyone wants to do this and is a noob like me, i found this pdf on extracting lactose, this is the one I will have a go at.



Attachment: Lactose.pdf (160kB)
This file has been downloaded 557 times

Rhodanide - 10-10-2017 at 09:04

You mean in school, or not?
'Cause if if you mean out of school then acetone peroxide (COUGH) I mean, Styrene from Polystyrene.

NEMO-Chemistry - 10-10-2017 at 09:24

Quote: Originally posted by Tetra  
You mean in school, or not?
'Cause if if you mean out of school then acetone peroxide (COUGH) I mean, Styrene from Polystyrene.

Trust me at the moment, one of those you mention would get you life in the UK at the moment!! lately some idot left some on a train.

Seems to be the goto chemical for getting 12 virgins, if you get my drift.

Styrene sounds like fun though.

Lactose is def first on the list though, will be doing this at the weekend, but might need to get creative with the solvent as i dont think i got much ethanol currently.

LearnedAmateur - 10-10-2017 at 09:25

Quote: Originally posted by NEMO-Chemistry  

Not sure i can get acetic anhydride, i will have to check. i am in UK and lately alot of stuff that was easy to buy 6 months ago is getting really hard. ADD sulphuric acid to that!!

esterification reactions look a good fit, as long as i can get/make the reagents. Thx anyway, you have given me a good list to research and get started.


You won't be able to get AA, not without being reported anyway (even only 30mL, which I've seen on eBay) but esterification can be done with carboxylic acids as well. The reason anhydrides are used is because the reaction isn't reversible - instead of water as the product of condensation, there will be a carboxylic acid which won't affect it in this case because acetic acid is competing with acetate which can then neutralised with a weak base. I haven't been able to find any ACS grade sulphuric acid but 96% drain cleaner does the trick in most instances and won't raise any flags.

Yeah, the good thing about them is that there are a lot of easily available reagents - I should mention that bulkier molecules are less prone to hydrolysis and less soluble in water so benzoic acid esters are a cheap and easy starting point. They are also safer than smaller esters and are commonly used as fragrances and flavourings, so that's another avenue you can explore.

NEMO-Chemistry - 10-10-2017 at 10:22

Quote: Originally posted by LearnedAmateur  
Quote: Originally posted by NEMO-Chemistry  

Not sure i can get acetic anhydride, i will have to check. i am in UK and lately alot of stuff that was easy to buy 6 months ago is getting really hard. ADD sulphuric acid to that!!

esterification reactions look a good fit, as long as i can get/make the reagents. Thx anyway, you have given me a good list to research and get started.


You won't be able to get AA, not without being reported anyway (even only 30mL, which I've seen on eBay) but esterification can be done with carboxylic acids as well. The reason anhydrides are used is because the reaction isn't reversible - instead of water as the product of condensation, there will be a carboxylic acid which won't affect it in this case because acetic acid is competing with acetate which can then neutralised with a weak base. I haven't been able to find any ACS grade sulphuric acid but 96% drain cleaner does the trick in most instances and won't raise any flags.

Yeah, the good thing about them is that there are a lot of easily available reagents - I should mention that bulkier molecules are less prone to hydrolysis and less soluble in water so benzoic acid esters are a cheap and easy starting point. They are also safer than smaller esters and are commonly used as fragrances and flavourings, so that's another avenue you can explore.


Great info thx.

i have around 500ml 98% sulphuric acid left. i treasure this :D
i have about 1ltr of 96% but its making the container go black!

I have also found what I think is a good site. I have loads of books on organic chem, but found them hard to follow, this site is helping to fill in the gaps, so in conjunction with the books i think i am making some progress in understanding it.

http://www.chemguide.co.uk/orgmenu.html#top

Rhodanide - 10-10-2017 at 11:02

Quote: Originally posted by NEMO-Chemistry  
Quote: Originally posted by Tetra  
You mean in school, or not?
'Cause if if you mean out of school then acetone peroxide (COUGH) I mean, Styrene from Polystyrene.

Trust me at the moment, one of those you mention would get you life in the UK at the moment!! lately some idot left some on a train.

Seems to be the goto chemical for getting 12 virgins, if you get my drift.

Styrene sounds like fun though.

Lactose is def first on the list though, will be doing this at the weekend, but might need to get creative with the solvent as i dont think i got much ethanol currently.


Left, as in "Oh, I left my Tupperware of AP and my diet soda on the train, I'll go back and pick it up and then proceed to dispose of it properly and safely, just like how it was made" or left as in... well, you know... (?)

Melgar - 10-10-2017 at 11:21

Nitroglycerin. At first I was extremely cautious with it, and tried detonating very tiny amounts. But the stuff proved surprisingly difficult to detonate. Nothing was doing it. I could light it on fire, it'd just burn. I'd mix it with the most reactive chemicals I cound think of, but the most I'd get would be NOx fumes. I put a few drops on a paper towel and started whacking at the wet spot with a hammer. Bam, bam, bam, bam, BAM!!!

My ears were ringing, thanks to having gone inside the shop where the anvil was, so I could use that. That was the first and last time I ever detonated nitroglycerin. I mixed the rest with acetone and water and sent it down the drain.

NEMO-Chemistry - 10-10-2017 at 12:05

Quote: Originally posted by Tetra  
Quote: Originally posted by NEMO-Chemistry  
Quote: Originally posted by Tetra  
You mean in school, or not?
'Cause if if you mean out of school then acetone peroxide (COUGH) I mean, Styrene from Polystyrene.

Trust me at the moment, one of those you mention would get you life in the UK at the moment!! lately some idot left some on a train.

Seems to be the goto chemical for getting 12 virgins, if you get my drift.

Styrene sounds like fun though.

Lactose is def first on the list though, will be doing this at the weekend, but might need to get creative with the solvent as i dont think i got much ethanol currently.


Left, as in "Oh, I left my Tupperware of AP and my diet soda on the train, I'll go back and pick it up and then proceed to dispose of it properly and safely, just like how it was made" or left as in... well, you know... (?)


Left as in...

I think I will dispose of this by using a train carriage to contain the blast. Really poor attempt as all it did was burn a little. The guy didnt even stay with it to collect his virgins.

Stuff that makes bangs in the UK, generally gets you 3 square meals a day for a pretty long time, all free of charge!

The Volatile Chemist - 10-10-2017 at 15:17

Hmm...I've yet to do too much OChem, but my limited history is below.

When I was 14, messed around with Haematein, making coordination complexes with it, and seeing what would happen when I mixed it with bleach, which I'd read was an oxidizer.

Messed around with vinegar/acetates for a while before I had an operating distillation apparatus.

When I first got my distillation apparatus working (was non-ground glass, liebig condenser w/ 250mL Dist. flask), tried to make concentrated acetic acid, which kinda worked. Distilled about 75mL 99% iPrOH after crashing it from the water w/ salt, then NaOH. Distilled another certain short-chain alcohol... attempted a iPrCl synth which pretty well flopped.

However, probably what I would consider my first real delving into OChem started late this summer when I bought 500 aspirin pills, and extracted the acetylsalicylic acid from some of them. However, first true organic reactions were refluxing of aspirin to make and crystallize salicylic acid, and the decarboxylation of it to phenol which I just completed three days ago. Lots of fun, would definitely suggest. However, super stinky and rather toxic (don't do it in your basement). My parents were not happy about the smell, to be certain...

Magpie - 10-10-2017 at 15:19

Benzene from NaOH and benzoic acid:

1. NaOH + benzoic acid + heat ---> Na benzoate + H2O

2. NaOH + Na benzoate + heat ---> benzene + Na2CO3



[Edited on 10-10-2017 by Magpie]

JJay - 10-10-2017 at 15:48

I think the first ever was Jones oxidation of aldehydes and ketones. First ever as a hobbyist... I did lots of extractions and distillations... first actual organic reaction as a hobbyist was bromination of something or other....

NEMO-Chemistry - 10-10-2017 at 15:57

In another thread i posted the woes of getting more than 24 aspirin tablets at a time in the UK, someone kindly posted a link where you can buy them by the hundred for dogs!! So aspirin is definitely on my to do list, mainly because it fits with my plan to make test kits with things like marquis reagent etc.

the main reason for this is, so i can identify components on a TLC plate from plant extracts.

Caffeine extraction is another i really want to do, i found an instant coffee thats totally undrinkable, but it costs around 38p!! for 150g. The tight arse in me really likes that idea. Although its likely this stuff contains little caffeine.

Benzene sounds interesting to do as well, and while i cant remember the experiments now, i have seen loads of experiments on you tube using benzoic acid.

I would need to look into the phenol thing, TBH i know nothing about it, but decarboxylation seems to be one of those 'must do' things in organic chemistry, alot like copper sulphate crystals are in normal chemistry :D.

Obviously at some point i will have to do a Grignard reaction at some point, as this seems to be the golden wings for a organic Chemist.

I had little interest in Organic Chemistry (well more the learning part) because i found it so difficult to understand. But finding that site i linked to earlier has made alot of things click. I think my sticking point was not having a clue what the drawing symbols meant. Again the site i linked to has made this much easier.

Funny how once something starts to click, it gets really interesting. Thx for all the suggestions, i hadnt expected it to fit so well with my general interests.

Melgar - 10-10-2017 at 22:41

Caffeine extraction is surprisingly easy. Its solubility in chloroform, relative to most of the rest of the stuff in coffee, is very, very high.

Rhodanide - 11-10-2017 at 04:53

Quote: Originally posted by NEMO-Chemistry  
Quote: Originally posted by Tetra  
Quote: Originally posted by NEMO-Chemistry  
Quote: Originally posted by Tetra  
You mean in school, or not?
'Cause if if you mean out of school then acetone peroxide (COUGH) I mean, Styrene from Polystyrene.

Trust me at the moment, one of those you mention would get you life in the UK at the moment!! lately some idot left some on a train.

Seems to be the goto chemical for getting 12 virgins, if you get my drift.

Styrene sounds like fun though.

Lactose is def first on the list though, will be doing this at the weekend, but might need to get creative with the solvent as i dont think i got much ethanol currently.


Left, as in "Oh, I left my Tupperware of AP and my diet soda on the train, I'll go back and pick it up and then proceed to dispose of it properly and safely, just like how it was made" or left as in... well, you know... (?)


Left as in...

I think I will dispose of this by using a train carriage to contain the blast. Really poor attempt as all it did was burn a little. The guy didnt even stay with it to collect his virgins.

Stuff that makes bangs in the UK, generally gets you 3 square meals a day for a pretty long time, all free of charge!



Not sure what you mean by "virgins" haha
Must be a British thing ;)

NEMO-Chemistry - 11-10-2017 at 07:23

Quote: Originally posted by Melgar  
Caffeine extraction is surprisingly easy. Its solubility in chloroform, relative to most of the rest of the stuff in coffee, is very, very high.

I was about to ask a question like this.

Because shipping is so expensive for my area, i tend to buy solvents in bulk, it cost the same to ship 10ltr as it does 500ml.

So rather than pay say £25 for ltr of hexane and £18 for shipping, i buy 5-10 ltr of it and still pay £18 shipping. Sometimes I get lucky and get 30 ltr of different solvents shipped together for £30.

Obviously this cost a fair bit, so i buy solvents once or twice a year. Currently all I have is IPA, petrol i can distill for Per ethers, Chloroform I can make from the IPA.

Methanol and ethanol mixed (very small amount at the moment). Maybe some others I could make. My next solvent order will be end of November.

most the extractions I seen use meth Chloride or DMSO (dont quote me I am having a bad memory day lol). So chloroform it is!

Actually I really like working with Chloroform. I might put my next chem order in early, I have use of an account with a chem supplier, the downside is min order value is pretty high.

The good news is its end of grass cutting season, so all left over petrol is now mine for the distilling :D. Mostly the lower fractions have all but gone by now, but I get stuff distill over from around 30-40C. i dont bother using anything that boils over 90C

Found a cheap online source for paracetamol, no idea what to with it, but a chem player video mentions it, so I will give that a go as well. Got loads of HCL so acid base extractions are high on the list.

Virgins I think are something from the old days, if where I live is anything to go by, then they died out with unicorns. We only got male ones around here..........No please dont ask how i know this lol.