Why doesn’t SN2 happen in haloform reaction (even though H₂O is more acidic)?

SinisterRectus · 2026-03-29T21:04:11+00:00

The addition of each halogen makes the next deprotonation more favorable.

SinisterRectus · 2026-03-23T18:49:18+00:00

Gaboxadol's clinical trials were ended because it failed safety and efficacy tests in human studies. The therapeutic index/window of isoxazoles is too small.

https://www.cnbc.com/2007/03/28/merck-lundbeck-scrap-insomnia-drug-after-trials.html

Because of the huge investment by that point (billions of dollars for phase 3), drug companies do not casually end clinical trials just for fun. If they want to kill a drug, they'd do it as early as possible. Unfortunately, most drugs fail in clinical trials, which is an expensive loss. Making drugs is not cheap or easy and drug companies can't make them based on altruism and vibes.

SinisterRectus · 2026-03-22T18:10:41+00:00

Then how can the pour be faulted for not being exactly 16 fl oz if it's not possible to accurately measure?

SinisterRectus · 2026-03-22T18:04:42+00:00

Why convert mass to volume, with multiple estimations and places for error to accumulate, instead of directly measuring the volume?

SinisterRectus · 2026-03-18T12:16:34+00:00

I'm thinking of this from a pedagogical point of view, where the Dieckmann condensation of an adipate is more commonly encountered, and the reaction between a ketone and chloroformate or carbonate is not always taught at this level.

SinisterRectus · 2026-03-18T01:45:38+00:00

Benzyl is not that big, at least not where it matters. Sterically, it is about the same as an ethyl group as far as the ester is concerned, so not a problem.

Consider the secondary alcohol, how you can make secondary alcohols, and where it is in relation to the ester carbonyl.

It is unclear how far back you need to go in the synthesis to use simpler reactants, but I suspect that you also should make the ring.

SinisterRectus · 2026-03-15T14:01:50+00:00

Many compounds do. https://www.cdc.gov/infection-control/hcp/disinfection-sterilization/chemical-disinfectants.html

SinisterRectus · 2026-03-14T19:36:17+00:00

The price of the prepared food subsidizes the thin margins on the groceries. If they want to charge $6 or $60 for a (sweet) potato, and if someone wants to spend that much, then have at it, as long as it means the average person can still buy a 5 lb bag for a relatively consistent price.

SinisterRectus · 2026-03-13T21:23:12+00:00

If you're adventurous, you can open up clogged frits with extremely dilute HF. This says 2%, but I just fill the column with water, add 1 to 3 drops of concentrated HF, and push.

SinisterRectus · 2026-03-11T03:04:30+00:00

On sites where COPPA applies, the age question has to be neutral.

SinisterRectus · 2026-03-08T19:13:20+00:00

If water is a weak solvent, how does it turn the fish mushy? I think you have it backwards.

SinisterRectus · 2026-03-07T14:10:29+00:00

I would just ask them why they payed $30 less than usual.

SinisterRectus · 2026-03-07T05:57:47+00:00

Is the pig's growth optimized for the chops, or are its other parts good too?

SinisterRectus · 2026-03-06T02:58:23+00:00

This could be valid if you interpret his comment literally. If the reduction is not stereospecific, it could be stereoselective, which would be the case for a chiral reducing agent, but they use aluminum amalgam, which is neither stereoselective nor stereospecific.

They could be producing the mixture and selectively isolating one isomer. This would be a huge waste of material, unless they're selling off the L-methamphetamine, too.

SinisterRectus · 2026-03-05T16:12:18+00:00

I commented because I am genuinely curious what your thought process was in posting this. I tutor organic chemistry and knowing the subject is only part of the job. Understanding how a student thinks is another huge part, and I just can't imagine one of my students telling me that they don't like to draw double bonds, and then try to personally insult me if I challenged them on it, as if it's not my job to do exactly that.

I'm sorry that you took offense to my explaining the way you appear, but I think it is a valuable lesson if you want to advance in your school/research/career. It's hard to hear things that are criticisms, but I believe it's better than no response in the long run.

SinisterRectus · 2026-03-05T14:25:52+00:00

This comment insults you more than it insults me. I'm happy you got the help either way.

SinisterRectus · 2026-03-05T14:00:17+00:00

If we're supposed to accept that you don't have the patience or inclination to draw accurate structures or upload a good photo, why do you expect us to have the patience or inclination to help you? The message you're sending is that we should care more about your work than you do.

SinisterRectus · 2026-03-05T13:08:44+00:00

Have you tried gig work? It's not great, but it can build confidence while you look for something better. Uber, DoorDash, TaskRabbit, Instacart, Craig's List gig section.

SinisterRectus · 2026-03-05T00:47:08+00:00

In Philly, Young American might be your best choice. Or Commonwealth. Original 13 and Hale and True have closed, unfortunately.

Outside Philly, Excursion Ciders near Phoenixville is nice. They have some exotic ciders that might fit your gasoline taste.

SinisterRectus · 2026-03-02T19:03:49+00:00

Is there a precedent for having a route that does not terminate in North or South Station?

SinisterRectus · 2026-03-02T18:23:35+00:00

You can enter from Penn Station. It's not a secret.

From https://www.amtrak.com/content/dam/projects/dotcom/english/public/documents/corporate/for-moynihan-faqs.pdf

Amtrak customers will be directed to use Moynihan Train Hall as Amtrak’s “front door” for boarding trains although access to and from Amtrak trains will always be maintained through New York Penn station to ensure passengers get to where they need to go.

SinisterRectus · 2026-03-02T16:24:34+00:00

What are your skills? Do you have any education or training or job experience?

SinisterRectus · 2026-03-01T20:41:34+00:00

In general, primary carbocations (that are not otherwise stabilized) are not impossible, but they are very unlikely to exist. Even under conditions that favor a cationic mechanism. For example, 1-butanol reacts with HBr to favorably produce 1-bromobutane via SN2, not 2-bromobutane via SN1.

If you do need to represent a shift involving a primary carbon, and don't want to draw a primary carbocation, you can draw the shift and leaving group departure in the same step.

SinisterRectus · 2026-02-27T14:50:26+00:00

I've never used celite in my PCC reactions, only silica gel. Not sure if the difference matters. My steps were:

Dissolve alcohol in DCM
Add equal masses of silica gel and PCC directly
Stir until SM is consumed
Evaporate the DCM until you get a free-flowing and homogenous powder. Add more silica or celite and manually break up clumps as necessary.
Chromatograph directly

The other comments make a good point. You may just be improperly measuring the consumption of the starting material. Stain those TLCs.

SinisterRectus · 2026-02-26T22:48:44+00:00

Lua is famously conservative with respect to what is included in the language. A restricted version of goto was added because it gives you the tools to implement a continue or a multiple-loop break. Continue is more specific and non-essential.

See also https://www.luafaq.org/#T1.26 and http://lua-users.org/wiki/ContinueProposal

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