> chemistry > physico-chimie > the-cinnamaldehyde-clock-nilered

How to make the Cinnamaldehyde Clock

NileRed - 2014-05-22

This is an interesting spin on the famous iodine clock reaction. Instead of a color change, there is a rapid formation of precipitate. 

Internet Schvitzing - 2015-12-29

You inspired me to go to school for organic chemistry. : 3

NileRed - 2015-12-29

+Internet Schvitzing yay! another one recruited!

Jack Shaw - 2020-10-12

Another one bites the dust.

Peer Vermeiren - 2020-11-25

so how is going there now 4 years later? I always likes chemistry but was afraid of the lot of math you had to do for it.

Therid - 2017-04-11

You might make me change my educational direction from Physics to Chemistry..

Therid - 2021-03-09

@J H Funnily, I actually did! I study chemistry at a university now! It's super fun, but there's a lot of side-subjects to go through too.

J H - 2021-03-09

@Therid Holy crap, that's awesome! Happy for you. I bet you're going to have a blast in this career. I wish I saw how much fun it could be when I was young enough. Oh well, I still do it as a hobby on the side.

Therid - 2021-03-09

@J H Is there no chance for you to switch course? I think I'll have a blast, too! I'm currently on my 2nd sem and we're still doing the basics of stuff, but I think it'll be rad when I specialise.

J H - 2021-03-09

@Therid I'm 33, and even though I had a great career as a Linux engineer (usually infrastructure engineer), I took a couple bad turns in my personal life after my dad died, and now I'm trying to get my career back on track. But as of now, I wouldn't be able to afford college (definitely could have before though, fml).
Maybe if I get my career back in gear and get a decent paycheck, I can entertain the possibility of doing some part time college.

Really though man, I may not know you, but I'm certainly happy for you. Glad you took the initiative to change your degree to something you will really like instead of getting complacent or just settling for something else.

Therid - 2021-03-09

@J H Ah shit man, I'm sorry to hear that. I can't imagine what it's like to lose someone close to you, but I do know how it feels to take a bad turn or two sometimes.
The fact that college has to cost money is a real shame, in my opinion.

I'm glad to have your encouragement! I, too, am happy to have changed to something that fulfills me more.

aienatu - 2017-07-13

bro, if you add a small amount of inert silica sand before adding the acetone, you can distinguish if the super saturation hypothesis is plausible. all the extra nucleation sites should alter the "clock" phenomenon. think about it.

NEY Industries - 2019-11-06

People really underappreciate quartz crystal timekeeping. :)

Sean Bailin - 2020-10-20

Dude this made me go out and buy orange juice. Also, it's cool to see an old NileRed video. You've come a long way, man.

ForeverMan - 2016-03-20

I like how you make this vids... I watch them all the time even tho i have no interests in doing this myself lol

NileRed - 2016-03-20

+ForeverMan I am glad you enjoy :)

Daniel Austin - 2015-11-18

could you get a similar aldol condensation reaction with vanillin?, i would guess you probably could

Ian Pogue - 2017-02-05

Would be really cool to see this reaction filmed with a really high speed camera.

siarles - 2021-03-16

Oooh, a different clock reaction. I've seen the iodine clock so many times I was starting to think it was the only one.

Peer Vermeiren - 2020-11-25

maybe it would be interesting to see this with a slow motion camera and right focus to see the first chrystals and then the chain reaction

sltflsh - 2015-12-14

What I didn't know there was an organic version of this reaction. I guess this works for other large aromatic carbonyls

Roy Roger - 2019-12-11

Very interesting to see, thank you for taking the time to make these videos!

MUDAMUDAMUDAMUDAMUDAMUDA MUDAMUDAMUDAMUDAMUDAMUDA - 2021-04-05

Damn. That looks like some delicious orange juice.

Daniel Bickford - 2019-05-15

Is the precipitate useful for anything

W4t3rf1r3 - 2015-07-14

I have a conjecture about why the precipitate forms. Perhaps the second aldol reaction cannot occur until the levels of the product of the first reaction is at a certain level compared to the concentration of acetone. Because the mixture is stirred, the entire mixture reaches this concentration at roughly the same point, with causes all the precipitate to form rapidly.

This is just a conjecture, as I know very little about this reaction, but I thought I'd share it.

Nakmus - 2014-05-24

Would a 2M NaOH solution work instead of the KOH?

NileRed - 2014-05-24

The purpose of the KOH is to deprotonate the alpha carbon for the aldol. NAOH is routinely used to do the same thing. So, based on that, I would assume that would be fine. I think KOH was called for just because it dissolves quicker in water.

This is not my final form - 2016-01-17

what type of experiments would you do in biochemistry?? please respond i LOVE your videos so much

NileRed - 2016-01-18

+marcel fernandez The classic experiment is to extract DNA from strawberries or some sort of meat. It's pretty cool to do.

Adam Harrington - 2016-01-20

+Nile Red If you're wanting to extract human DNA, semen contains a lot of DNA in it, far more than blood. Maybe do that bit off camera though, eh.

NileRed - 2016-01-23

@Adam Harrington haha i think ill pass on using that as a source!

TheRedKnight - 2016-03-02

+Nile Red Do an experiment using vanadium bromoperoxidase

Mika - 2020-02-24

The thumbnail
What the doctor drink after the pee test.

Archis - 2017-02-19

Can you do this reaction using cinnamon powder or using a filtered ethanol extract of the same?

Objects in Motion - 2019-04-03

No

robinhooodvsyou - 2014-05-23

Do you know if there`s any uses for the precipitate ?

NileRed - 2014-05-23

I did my best to try and find some sort of use, but I was unable to find anything.

Kitsune Fox - 2015-03-26

@Nile Red @robinhooodvsyou Dicinnamalacetone (aka 1,9-Diphenyl-1,3,6,8-nonatetraen-5-one), the precipitate is sold by both Sigma and Acros Organics (Thermo Fisher Scientific).
Sigma claims that it was used as an indicator in measuring the surface acidity of homoionic montmorillonites (a phyllosilicate mineral). Also that it can be used as an indicator (turning yellow to bright red) for detection of excess hydrogen halides in many organic solvents (but not alcohols). As for uses in an amateur laboratory, I can't find anything either yet.

Ari Binu - 2019-03-22

It is dibenzalacetone or curcumine like compound, perharps it can be used as sunscreen or antioxidant too

The Bomb - 2016-05-29

That result of this reaction looks exactly like the lead nitrate and potassium iodide reaction.

정명진 - 2017-05-26

so what did KOH really do in this experiment? I assuming that when Cinnamaldehyde reacted with acetone it formed single conjugated product, and the product combined with OH-? If so, what is ethanol for? I really love your video and this lab. I am trying to simulate it at school tomorrow, so please help me. Thank you

javier alvarez - 2018-02-26

Hello have you got a fumme Hood? please can you tell me about where are you bought the fumme Hood or make video about that how to make a  fumme Hood please

BackYard Science 2000 - 2019-06-08

There are many, many videos on YouTube about building your own fume hood. Buying one would be fairly expensive.

Brandon Haldiman - 2015-11-17

can this be done without constant stirring once the acetone is added?

NileRed - 2015-11-18

I am not sure. I have never tried it without stirring thoroughly

Lenka Ubauba - 2019-01-16

I don't know much about organic reactions, but why is there that aceton

Muonium-235 - 2019-02-23

Listen the video maybe?

Nokia n900 - 2020-07-11

This is a different kind of reaction video.

Mystic Virgo - 2017-04-29

Looks to me that that second step in the reaction makes a product that MIGHT be polymerizable ..

Sing Lau - 2019-03-24

If it is a clock reaction with repeatable time, I assume it is due to homogeneous nucleation that caused the precipitation. Are there any explanations why the rapid stirring/ irregularities of the apparatus do not cause heterogeneous nucleation to take over, like when shaking super-cooled water?

aienatu - 2017-07-13

one more thing, my brother. how's about you read up and try to do an oscillation reaction. there are a few which have been described. there's one with iodic acid. holla at yo boi!

Revelde20 - 2016-01-24

so what is the ppt??

BackYard Science 2000 - 2020-01-05

Go to 1:43 as it is written out in the equation above the reaction. It is a very long name and now I understand why he didn't name it.

illya.ruslanovich Shevchenko - 2020-12-09

C6H5-CH=CH-CH=CH-CO-CH=CH-CH=CH-C6H5

deepstrasz - 2019-01-16

Orange juice.

Christina - 2020-07-12

Forbidden orange juice