I saw a YouTube video of a chemist using the minty lifesavers to convert to salicylic acid.

I am trying to recreate it using three different methods to extract the methyl salicylate and then do the reflux to get salicylic acid.

Procedures I used: https://docs.google.com/document/d/112Ltfo4i5kAadg61ixL56L_A2-uW3kxAZpB6H_uOGaw/edit?usp=drivesdk

I’ve added more acid than necessary and still no crystals formed after putting it in an ice bath and scratching the flask for over an hour. They’re covered with a watch glass in the fume hood, but any troubleshooting advice would be appreciated!

Hi! Im stuck on the pushing mechanism for this pathway. I thought the C6 H would get stolen, but a triple bond in the benzene ring feels absolutely wrong.

So basically I was doing a synthesis of some molecules for their Anti-cancer activity. I was going to follow the Bucherer bergs hydantoin synthesis. So basically in the first step I will synthesize the hydantoin ring from the ketone (acetophenone derivatives) and then add another acetophenone at the N-3 of the hydantoin ring. So at first I tried only acetophenone instead of derivatives for a trial reaction. Everything went well until the first step. The problem occurred in the 2md step. Basically there should be a leaving group attached to the alpha-methyl group of the acetophenone for the fusion to form the final compound. So how am I supposed to do alpha-halogenation of acetophenone derivatives. My derivatives are given in image. So how should I proceed to halogenate the alpha-methyl groups of those derivatives. And even after alpha-methyl halogen will that still get fused to the N-3 of the hydantoin derivative that I will get from 1st step. Generally a halogen electrophile will work, so can I use bromine water for that. My predicted mechanism is given in the 2nd image. Please guide me guys!!!

my teacher taught in a more organised way regarding mechanisms of named rxns. case 5 here means migration of hydride ion occurs and case 4 is ɑ-H taken by base. so this is the mechanism i thought of but there's a twist.
the answer is the other one(without mechanism)
when i asked him on telegram, why? he replied that oxidation of -OH groups will occur first but i dont get it why will it occur first when hydride migration takes more effort that ɑ-H abstraction

all i see on how to figure it out is memorizing what nucleuophile, base, and substitutes combo leads to each but memorization is so much more difficult for me in comparison to understanding. anyone have a method of understanding when each one happens.

I would imagine it's some type of AI, no? I don't know if it's generative AI, but it'd have to be some sort of AI, I would imagine.

I've always been curious how they work.

I came up with this problem myself and brought it to the organic chemistry professor I TA for. I initially thought this would be S. The chiral carbon has connections to the oxygen and hydrogen so I know those are atoms 1 and 4, respectively (1->4 being highest-> lowest priority). The two other atoms are carbon so I first compared the path of the higher priority atom - oxygen, and since a difference isn't found in what the oxygens are directly attached to (not looking at the whole chain), you look at what the lower priority atoms are attached to (the bottom carbons), which we do see a difference and would prioritize accordingly (left carbon as 2, right as 3, counterclockwise with lowest priority = S).

My organic chemistry professor said that carbon would actually be R since you first have to look and compare the entire chains coming off the higher priority atoms first before going to the carbons. Since the oxygen on the right has a Br at the end that right carbon would actually be 2 instead of 3, making it clockwise and thus R. But he said he was "pretty sure" and didn't seem 100% confident.

Can someone please confirm for me the right answer? Thank you!

Fischer projections make no sense to me. The correct answer for the first image is B and the correct answer for the second imagine is A. The approach I try to take when creating the projection from the wedge-dash bond line structure, is that if you have a wedge pointing upwards then you would flip the side. If it’s a dash, you keep the group on that side. This approach works for image 2- you have an OH wedge on your left, so you would flip it in make it on the right on the Fischer projection. Then you have a F wedge on your right, so you flip it and make it left on the projection. Finally you have a Cl dash on your left, so you keep it left on the Fischer projection. However this doesn’t work on image 1, you have an OH wedge on your left so you would make it right on the Fischer projection. But answer B doesn’t show this?

sp?? 🤔

in deciding which direction the equilibrium lies, we are to draw out the conjugate bases of each of these. doing this reveals that the conjugate base of the molecule on the left has a lone pair that can participate in resonance, which stabilizes the molecule significantly and so we say that the equilibrium lies to the right.

but why can't we just look at the acids directly and compare their strength? it seems to me that since the formal charge - sigma - pi pattern exists on the left acid, there should be resonance. i've had someone try to explain that it's because oxygen has a full octet and so it cannot act as an acceptor of electron density? but there are other questions wherein atoms with full octets can participate in resonance. i don't really understand how to approach resonance in general i think.

ETA: another question: when we say that the lone pair in the conjugate base can participate in resonance - are we not considering that doing this would disrupt the aromaticity in the ring??

Hey everyone!

I'm working on translating a condensed structural formula into a skeletal/bond-line drawing:

For example, in a chain containing a -CF2- group (like CH3-CH2-CF2-CH3)

For the CF2 group:

If I keep the carbon as an unlabeled vertex in the main zig-zag chain and draw two straight vertical single-bond lines (one pointing straight up to an "F" and one straight down to an "F") directly off that carbon vertex, is that acceptable standard convention? Or are there specific angle/wedge rules I should follow when representing a difluoride carbon in skeletal structures?

Thanks for any clarification on drawing conventions!

Good afternoon. I work in medicinal chemistry, but my main focus is small-scale (milligram) organic synthesis. I’m looking for a more up-to-date book on synthetic methods (amidations, reductions, SNAr, etc.), something that covers, for instance, various ways to reduce a benzonitrile. Has anyone here bought The Chemists' Cookbook? Or is there a better option for my needs? I'm open to suggestions.

I'm assigning the aromatic region of two 1,3-disubstituted benzenes (A and B are different groups). Both were run at 400 MHz in DMSO-d6. They're from different analogues, and the bottom spectrum is better resolved. Are the assumptions I've made in the image fair?

Coupling constants from the bottom spectrum:

8.22 (t, J = 2.2 Hz), H1

8.00 (ddd, J = 8.1, 2.2, 0.8 Hz)

7.84 (ddd, J = 8.2, 2.1, 0.8 Hz)

7.68 (t, J = 8.2 Hz), H3

The coupling constants of the two apparent triplets led me to assign them as H1 and H3. What's bugging me is the intensities as none of the patterns are symmetrical, as you'd expect from first-order splitting.

Should I report these as t / ddd / ddd / t, or is multiplet more appropriate given the asymmetry?

H2 and H4 have identical coupling patterns, so I think I'd need NOESY to tell them apart.

My thinking is that second-order effects mean I can't say for certain which peak is which from the coupling constants alone. My assignment seems to fit, but it would need 2D NMR to confirm. Is this correct?

Thanks!

Mine's benzene. The structure is found in SO many chemicals, and its very representative of organic chemistry to me.

I'll accept ANY structure, not just functional groups.

Edit: I LOVE BASKETANE

the acidity of three cyclic compounds:

(i) Pyrrolidin-2-one: 1 carbonyl, 1 NH

(ii) Succinimide: 2 carbonyls, 1 NH

(iii) Hydantoin: 2 carbonyls, 2 NH groups

The Paradox:

Expected Order: (ii) > (iii) > (i)

Standard resonance logic suggests the extra nitrogen in hydantoin (iii) causes cross-conjugation. This should weaken the electron-withdrawing pull of the carbonyls, making its conjugate base less stable than succinimide's (ii).

Experimental Order: (iii) > (ii) > (i)

Real pKa data shows hydantoin is actually more acidic than succinimide.

Discussion Questions:

Why does the empirical data contradict standard theoretical predictions? I am looking for the decisive factor driving this inversion:

Inductive Dominance: Does the strong inductive pull (-I) of the second nitrogen simply overwhelm its destabilizing cross-conjugation (+M) effect?

Conformational Isolation: Is the second nitrogen sterically forced out of the plane of the ring? If it is non-planar, cross-resonance would be impossible, leaving the -I effect as the sole influence stabilizing the conjugate base.

Looking for clear mechanistic insights from advanced organic chemistry researchers or students to settle this.

Is there anyone from Uvic Msc/ PhD currently enrolled? I got some questions to ask. Please DM.

I am at my first year as a chemist teacher told us to make different formula with C6H6 and i got this i didn't understand if it right or wrong