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Tlc Crime

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Tlc Crime

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Tlc Crime

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Most organic compounds, which have a minimum of conjugation will be observable in this manner. Those are generally highly aliphatic compounds with little functional groups.

Staining agents for TLC are basically solutions of one or more compounds in which we can dip the plates after elution. It is worth keeping in mind that, even if your target compound s absorbs strongly UV or even visible light, it is recommended to stain the plate anyway, if you can.

This is because there might be other components of the mixture present as impurities which you cannot observe correctly under typical UV-Vis conditions.

So remember, even if your compound is visible at first sight, check also under UV light. And even if you can see everything under UV light, developing the plate with a general-purpose staining agent will almost never be overkill.

Now follows a list of the most typical staining agents, and how to prepare them. There are many others, some incredibly specific for certain types of compounds.

Many people use this vanillin solutions. It is really easy to prepare, and after heating, it is really sensitive to most functional groups.

The coolest thing is that many times, small changes in functionalities on organic compounds lead to a change in the color of the TLC plate after vanillin staining and heating.

This is really great if your starting material and product have a very close Rf. You can still differentiate them by the color!

Specifically, it shows brightly most compounds with polar functional groups. It might not be great for highly apolar compounds, such as simple alkenes or aromatics.

The recipe for this stain is really easy: Weigh g of vanillin, dissolve it mL of ethanol, and add 2. Stir and you are good to go!

To use it just dip your eluted TLC plate, and heat up with a heating gun. This is another great general purpose stain.

It is my personal favorite, and it does color almost anything you can find in an organic chemistry lab. From polyaromatics to alcohols, going through alkenes, or simpler aliphatic compounds.

It gives you different blue-green shades, so it might not be the best for identifying different compounds with similar Rf, but for first choice, it will do great.

This staining solution is also extremely easy to prepare. You just need to dissolve around 5 g of phosphomolybdic acid buy the lesser quality one for this purpose!

This is the most classical one, probably the cheaper option, and it is also quite general. Basically it turns your TLC plate purple, and every compound that can potentially be oxidized will show up as a yellow spot.

You basically need to dissolve 1. Just be careful not to stain yourself with the mixture! It is a water based stain which makes your spots turn blue over a cool pale yellow background, after heating.

I have seen people use two different recipes. Dissolve 5 g of ammonium molybdate and 1 g of cerium sulfate OR 2 g of cerium ammonium sulfate into mL of water.

To this mixture, add 10 mL of concentrated sulfuric acid, and stir! There are many other staining agents, but they are usually more specific for certain types of compounds, and not the best ones to prepare or use routinely in the lab.

To anyone with a couple of years of experience in the lab, choosing the solvent combination for running a TLC or a column comes really easy.

Or at least a good starting point. But for beginners, it can be really overwhelming. After all, there are a lot of different functional groups, and A LOT of different combinations.

Not to mention the endless solvent combinations that you could imagine. That is the reason why it is extremely difficult to find a good guide out there to choosing the eluent for chromatography.

We wanted to get as close as possible to the best guide. And we came up with the following infographic for choosing solvents for TLC.

Keep in mind that of course this is an orientation and approximation, and there will always be compounds that behave weirdly.

But we think that it will do the trick to for most situations, at least as a first shoot for a new reaction that you are running.

We have limited it to classical mixtures of apolar solvent hexane, pentane or cyclohexane and polar solvent ethyl acetate or diethyl ether , as a combination of these solvents will be usually enough to deal with most organic compounds.

Again, this is an approximation, and the values are not always additive. But if you have 3 alcohols, it is not certain that will work. Maybe is enough.

Or maybe not even , maybe you even need to add methanol. As you can imagine, the most polar group itself will often dictate the polarity of the entire molecule.

Then you change that methoxy group for an alcohol. For practical purposes, solvents such as pentane, hexane, heptane or cyclohexane are similar, polarity-wise.

The only problem with those two solvents is that are less volatile, and more difficult to get rid of. If you need a more volatile alternative, use pentane.

This should be used in cases where your target compound is relatively volatile and you cannot put it under high vacuum to remove the solvent completely.

In the polar component side, ethyl acetate and diethyl ether can be the main options. Diethyl ether is more volatile, so it should generally be avoided if possible, unless it gives you a much better separation or your target product is also volatile.

This can potentially lead to reproducibility issues. Compounds with basic or acidic sites, such as amines, amides basic or carboxylic acids acid , can sometimes stick to the silica gel of the stationary phase a little bit too much.

This results on very wide spots on TLC, and as a consequence, very broad bands in your flash column chromatography purifications.

This deactivates de acidic sites of the silica: Si—O—H bonds. By adding Et3N to your eluent, you remove all of them and your compound will elute freely!

Similarly, acidic compounds such as carboxylic acids can react with Si—O bonds in silica gel to give Si—O—H, which really makes them stick to the stationary phase.

This will make acidic compounds much more mobile through the TLC plate or column. We have already covered flash column chromatography in a previous section.

Running purifications is one of the main applications of thin layer chromatography. But we can actually apply TLC to run preparative-scale purification.

Well, preparative TLC is just a regular thin layer chromatography separation, but with a bigger plate! They are usually made of glass coated with a thicker layer of silica gel.

Then, instead of a single point spot, you apply the solution of your mixture in roughly 0. For applying this solution, I usually use a 1 mL syringe with the thinest needle I can find.

It has to be uniform and you need to be careful not to scrap the silica! After drying it, you elute the plate in the appropriate solvent system carefully chosen by classical TLC , and the different compounds will get separated.

You obviously will need a bigger chamber. Afterwards, you just need to scrap off separately the bands that you are interested in.

For this, visualize the plate under UV light, and mark with a pencil the bands you are interested in. Then, scrap off the band, and just pass a polar solvent such as DCM through the silica gel with your product, so it gets dissolved.

Filter it off to get rid of the SiO2. All this being said, I will leave you with a short time-lapse video of how does running preparative thin layer chromatography go:.

TLC is a simple yet widely used technique. So in most reports and journals, you should provide information about TLC data for experimental procedures.

The very minimum is stating in which solvent mixture you have run the purification of each compound. The best way, is reporting retention factors Rf of your product in a certain solvent mixture.

For example, you report a procedure to make benzaldehyde. We will finish by gathering some tricks, tips and lab hacks for TLC.

You will definitely find something useful here! Two-dimensional thin layer chromatography or 2D TLC got me through my first year of grad school, when I had to work with a great deal of compounds that could potentially decompose during purification on silica gel.

We have covered this sand bed for TLC in our lab hacks post. If you have trouble leaving your plates standing vertically on your elution chamber, of if you want to run many plates on the same eluent at the same time… Get a big enough chamber, and make a bed with sea sand at the bottom about 2 cm is enough.

Then, put your eluent in the chamber covering just a bit above the sea sand, and stick all the TLCs you need on the sand!

They will not fall, and you can elute many of them parallel to each other. Letting your plate drawn will result in spot broadening and worse separations.

Huge spots appear when you overload your TLC plate. Dilute more your sample before spotting. Some compounds can decompose when passing through silica gel from TLC plates or columns.

You can tell if a compound is stable by using 2D thin layer chromatography see above. No, you should always spot the samples slightly above the level of eluent in your TLC chamber.

Otherwise, you will dilute the spots and worsen your separation. Spot both the starting material and the reaction mixture in your TLC. Also, make an additional spot with both starting material and reaction co-spot.

If the reaction is finished, you will see two different spots snowman shape in the co-spot, even if the Rf of both compounds is the same. The most important thing is to report the retention factor Rf in a certain eluent combination, of all the compounds that you have used.

Alternatively, you can draw the TLC in your lab report. The retention factor is the distance that a compound travels through the silica plate respect to the total distance the eluent front has moved.

The typical eluent for TLC is a mixture of an apolar solvent typically hexane or pentane and a polar solvent dichloromethane, diethyl ether or ethyl acetate.

Top sum up, o matter if you are new to synthetic chemistry or an experienced researcher, we hope you have learnt something from it! So please, head right into the comment section, and ask whatever you want.

Remember that there are no stupid questions. Any criticism and suggestion to improve the guide further will be highly appreciated.

If you think that something is missing, or not well explained, go for it. Finally, if you found this guide useful, please, feel free to share this on your websites, with your students or colleagues, or anywhere you like.

Gigantic work. I think it should be worth teaching in advanced org chem practical courses. Maybe in smaller labs this is less practical, since some of them remain less used and just dry out.

If I had to choose one it would be phosphomolybdic acid. Second running up acidic vanillin. How to identify in TLC by comparing the Rf value of sample and reference standard?

How is tolerance range? To do this you run a TLC with a co-spot. This means, you do three spots on the TLC: one with the sample or reaction mixture , another one with the reference standard and another one usually in the middle , in which you spot both your sample and your reference.

The you elute the TLC. If the compound is exactly the same, you will only see a single spot in the co-spot.

If you see two closely overlapping spots snowman shape , that means that you have two different products. Like this you can usually resolve products with y Rf differences as low as 0.

Also, staining the TLC afterwards with solutions such as acidic vanillin or PMA, often allow to see different compounds in different color shades.

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TLC of black ink. Credit to Natrij via Wikipedia. Table of Contents hide. Step by Step Guide 3.

TLC of a plant extract. Separation of two main components of a mixture pink spot and red spot. Credit to Lisa Nichols via LibreTexts.

Typical TLC size and arrangement. Spot the TLC mixtures at the corresponding mark in the line above the bottom of the plate. Then elute the plate and see how many compounds there is in your mixture, and how polar are they, just by checking out the different spots.

TLC spots before, at the bottom, and after elution, at the top. TLC eluting in the solvent chamber. Credit to SiliCycle.

How to determine retention factor Rf in TLC. Infographic guide on how to set up, run and analyze a TLC. Click on the image to expand.

Basic way of monitoring reaction progress by TLC. Flash column chromatography purification. Credit to Dr. Jessica Torres. TLC chambers designed for that purpose.

TLC chamber made with a beaker, a watch glass and filter paper. Credit to CU Boulder. A glass tar with a cap makes up for a great TLC chamber.

TLC stained with acidic vanillin. Graphic guide to choose a eluent starting point for TLC. Different compounds after a prep TLC separation. Then you just need to scrap the band of the compound that you want, and elute the compound from the silica, filtrate and concentrate.

Do you develop the TLC plate all the way to the top? How do you fix big spots on TLC? How do you know if a compound is stable on silica gel?

Should you spot TLC samples right at the bottom of the plate? How do you TLC extremely polar compounds? How do you know if a reaction is finished by TLC?

How do you report thin layer chromatography? How do you calculate retention factors on TLC? What solvents do you use in thin layer chromatography?

Comments Gigantic work. Out of the most common stain mixtures, which one would you choose first for general purposes?

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TLC shows are really something. With over original programs under its belt, there's no denying the network's ability to keep millions of people interested, entertained, and coming back for the content they crave each week.

However, the TLC viewers know and love today is a far-cry from what the network was originally intended to be. True to its name, TLC's earliest days were focused on educational programming , with the network airing documentary series on topics like space and paleontology.

While viewers might learn a thing or two while binging their current TLC favorites, the network now boasts a steady stream of reality programs showcasing psychic moms, flashy weddings, and pregnant teenagers.

Here's a list of the TLC shows worthy of a good binge — as well as those you might want to skip. One of the best TLC shows is I Am Jazz , a reality show following the life of Jazz Jennings — a transgender woman who quickly rose to prominence in when Barbara Walters famously interviewed the then 6-year-old Jennings.

While I Am Jazz centers around a transgender person, it doesn't aim to exploit or sensationalize the transgender community. As Time magazine noted in its review of the show, " I Am Jazz [chooses] to teach to the curious rather than preach to the converted.

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As viewers of the show have noted on social media, the shower scenes that often appear at the beginning of each episode are unnecessary and uncomfortable for everyone involved.

Commenting on Reddit , another viewer of My lb Life revealed they found the shower scenes difficult to watch, writing, "I'm sure when the show first came out, they were enticing for viewers with that morbid curiosity.

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My tear ducts get a good cleansing with every episode. Even celebrities aren't immune to the heartwarming series, which often features adoptees being reunited with their biological family members.

While a K-1 visa is often associated with immigration fraud, Lenni B. The series first premiered in March , introducing the Roloff family to the world.

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He continued, "We're going through our own particular challenges. But this is without a doubt the most in-depth look at dwarfism.

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However, some mental health professionals think the show's portrayal of hoarders was exploitative and disagree with the program's way of "fixing" the problem by forcing the hoarder to simply get rid of their stuff.

There's no question that society has an obsession with marriage — or, more specifically, the act of getting married. Witty and welcoming, Fenoli rarely fails in his quests to find the perfect dress for a bride.

In an interview with The New York Times , Fenoli likened his work to that of a therapist, saying, "A therapist doesn't tell you what to do, and I don't tell the brides what to do.

I guide them. With minimal drama, touching glimpses inside the lives of brides-to-be, and dozens of dazzling dresses to behold, this show is a light-hearted, fully entertaining watch — even if you're totally over the seemingly year-round wedding season.

According to TLC's website, Unexpected is a series that takes a "raw" look at three pregnant teenagers and the effects their pregnancies have on their families.

If the premise sounds familiar, it's probably because it is. She continued, adding, "I think it's more real. I feel like our stories are better.

Still, it's difficult to watch Unexpected without feeling like what you're seeing has all been done before. And, in the era of peak TV, is it really necessary to expose the private lives of pregnant teens in the name of entertainment?

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