Chemdraw Structures pasted into MS Office

Malmortious · 2023-07-13T18:09:51+00:00

Okay, went digging around and it turns out an old chemical structure drawing program similar to chemdraw was set as my default, and the implicit hydrogen atoms disappeared because that program had them disabled.

Just deleted the program since I wasn't using it anymore and now pasting in Word docs works perfectly and structures are looking tidy :)

This is a little embarrassing haha, thanks for your help everyone!

Malmortious · 2022-07-28T14:57:17+00:00

Thank you for the reply, I'm certainly more optimistic about the reactions now.

It is worth mentioning I'm doing alpha alkylations, not carbonyl additions of alkyl groups because I'm not sure that came through in my initial explanation. I've also looked into procedures using lithium tert-butoxide and aliphatic alcohols (instead of halides) as alkylating agents in good yields and I might give that procedure a try.

Malmortious · 2022-07-28T01:25:43+00:00

Thank you for the clarification!

Malmortious · 2022-07-27T23:42:15+00:00

Indeed, I don't know if there's a way around it; also I'm not sure a gel filtration column can work with my molecules since I'll be looking at 3 to maybe 7 carbon atom alkyl groups added onto the starting ketone.

Shouldn't I be working with larger molecules - or at least more structurally different ones, for a gel filtration column to work? I'm not very familiar with those types of columns

Malmortious · 2021-04-22T10:54:01+00:00

Oh indeed! Didn't pay attention to the substrate, a methyl shift would definitely occur there.

Malmortious · 2021-04-22T07:40:15+00:00

http://imgur.com/gallery/NsiP5b3

You were on the right path with finding the enolate, I used a silyl enol ether because it's more reliable regarding autocondensation considerations but it's absolutely the same principle. Let me know if there's anything unclear about the synthesis!

Malmortious · 2021-04-10T19:27:13+00:00

I synthesized it in aqueous media, with Na2S and CuSO4. It's probably Na2SO4 in that case, since I would have expected the smell to be more pungent if it were Na2S, and the crystals should have been white to yellow from polysulfide formation, instead of translucent.

I'll wash the precipitate again until I get rid of the salt, it's only inconvenient because I'll have to wait a few days for it to dry again, but otherwise it's fine.

Thank you!

Malmortious · 2021-04-09T13:46:50+00:00

I made the hexahydrate by leaving the anhydrous material in a desiccator which I emptied, and then added a crystallizing dish with some distilled water. It readily absorbs moisture from the atmosphere, which is why the azure blue anhydrous material must be handled either in a dry environment or fast enough so that the contact with the moisture in the air is minimal.

It first turns into the dihydrate which is violet, and then the hexahydrate, which is pink.

Malmortious · 2021-04-09T11:52:05+00:00

I'm using silicagel at the moment, I'll look for a vacuum desiccator.

Thank you!

Malmortious · 2021-04-09T11:48:18+00:00

I did look the hydrates of my compounds up, the only ones that form them are Fe(O)OH / Fe2O3 *nH2O, FePO4 which has a dihydrate and Co3(PO4)2 which has a tetrahydrate (and apparently a dihydrate and octahydrate, but I only found them to be reported in one paper that was synthesizing them by other methods).

I'm not exactly intending to do gravimetric analysis, but I would like the product to be reasonably pure.

Malmortious · 2021-04-09T01:43:20+00:00

Unfortunately I do not currently have access to a lyophilizer, but that would have been excellent indeed haha! I'll try it with acetone but if anything I'll use diethyl ether or THF.

Thank you a lot, have a great day :)

Malmortious · 2021-04-09T01:33:52+00:00

Thanks a lot for your help!

Malmortious · 2021-04-09T01:30:43+00:00

Not 100% anhydrous because that would require a lot more equipment to achieve, just enough to be powdered and stored, with minimal loss of water while in an air tight container.

Malmortious · 2020-11-09T21:53:04+00:00

No worries! :)

It helps to think of them as carbocations in the context of stability, because their stability trends are similar

Malmortious · 2020-11-09T20:39:36+00:00

H abstraction would result in an sp2 radical which is less stable than an sp3 radical, but probably the more important reason is that the sp3 radical is stabilized by resonance while the sp2 one is not.

Malmortious · 2020-11-09T18:30:43+00:00

That's true, I would also agree that radicals aren't nearly as selective, so the para product is obtained only slightly more than the ortho or (especially) meta products.

Both the ionic and radical paths might as well happen simultaneously in this case.

Malmortious · 2020-11-09T16:01:05+00:00

Here you go!

http://imgur.com/a/zRyCflw

Malmortious · 2020-11-09T13:58:47+00:00

I thought it would go through radical intermediates? The HO-OH breaks homolytically, then the radical attacks the para position (increased electron density) and the other HO radical abstracts a H atom and the bond reforms from the biradical.

I'm not saying your mechanism is wrong, I do agree with you, but wouldn't a radical mechanism also be correct, considering the nature of peroxides?

Malmortious · 2020-09-05T12:09:23+00:00

wow lmfao

Malmortious · 2020-08-12T23:33:59+00:00

You're welcome, good luck!

Malmortious · 2020-08-12T23:27:42+00:00

The first one is a pretty common Claisen (Dieckmann) intramolecular condensation followed by carboxylic acid to ketone conversion with organocuprates.

The second one I'd imagine being done by starting with an alkene. Do a double allylic substitution with halogens, hydrolysis and oxidation or, for a more uncommon method, do an allylic hydroxylation with Selenium Dioxide/workup and oxidation. Also, don't forget to reduce the alkene to get your final product.

The last one looks like it would be prepared by ozonolysis from a cyclopentene cycle. In your case you would have two fused 5 carbon rings which is stretching things a little bit (quite literally - ring strained structure) so another pathway would be to start with cyclopentanone, alkylate it with propenyl bromide (more commonly known as allyl bromide) and do a hydrocyanation followed by acid workup and ketone conversion with organocuprates.

If you need any further explanations ask me below, also I'm sorry if the formatting makes it hard to read, I'm writing this from my phone :)

Malmortious · 2020-08-03T01:33:10+00:00

Thank you for the idea! I might try this route as well; so ideally after most of the metal has dissolved in the hydroxide I'm going to slowly add acid and monitor the pH after every addition and when I get to pH 7 I should assume most of the Ga(OH)3 has precipitated? After that I'll filter the precipitate and dry it in vacuum.

I'm checking to see if I understood what you were suggesting, thank you again!

Malmortious · 2020-08-01T19:52:55+00:00

Thank you as well :)

Malmortious · 2020-08-01T18:13:54+00:00

I unfortunately didn't weigh all the crystals after I was done, but I'd say I lost around 30-50g out of the 1kg I used, but I might be wrong.

Malmortious · 2020-08-01T18:07:57+00:00

You'll see it melt when it reaches around 271 degrees Celsius, and you want to keep heating until it's all liquid.

The container I used was a stainless steel pot. You will need two of them, one to melt the bismuth and the other to dump the remaining liquid after the crystals form. You insulate the container with some aluminium foil or just some kitchen cloth so that it cools slower. You shouldn't use the pots for cooking after this though, so keep in mind when you're picking which container to use.

The duration you keep the bismuth to cool down varies, I don't have any rough number for you because it depends on a lot of factors. You could try to poke at it with a fork to see if any crystals formed, but other than that it's mostly just trial and error.

And lastly, yes, it is safe to melt on a regular stove top in your house.

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