Enolates (& their equivalents) are one of the cornerstones of many a good synthesis. So here is a #Chemistry #ChemEd #ChemSky intro to their formation & general reaction. More details on the aldol reaction & enolate equivalents will be in subsequent summaries. Enjoy.

The 1st of a few #ChemEd #Chemistry #ChemSky summaries related to enols/enolates/etc. This one covers keto-enol tautomerization and two reactions of enols. As always, it is just meant to cover the basics. It is a summary to refresh/support students' memories. As such, I hope it is of some use.

The obligatory summary of a summary and a table of E1 vs E2 vs Sn1 vs Sn2. Hopefully, this is of use to some, but if I'm brutally honest, it was just a quick stop gap while I work on more fun #ChemEd #Chemistry #ChemSky summaries (currently writing ones on cycloadditions and rearrangements). Cheers

The obvious follow-up to SN1/SN2 substitution is a #ChemEd #Chemistry #ChemSky summary on E1/E2 elimination. This summary only looks at E1/E2 & not fun like E1cB. More detail is www.makingmolecules.com/blog/elimina.... Enjoy (& yes a summary of which mechanism operates is coming next week). Enjoy

Today's #Chemistry #ChemEd #ChemSky summary is SN1/SN2 substitution. I waited until 46th summary to cover this as I don't think it's as important as the chemistry of the carbonyl group (but is invariably introduced 1st in textbooks 🤷‍♂️go figure). More info www.makingmolecules.com/blog/substit... enjoy

A contentious #ChemEd #Chemistry #ChemSky summary covering rates of reaction. It is the textbook version & is wrong if you understand kinetics ;) I'll add references showing why as a reply. It's here as most UG still learn it. Hopefully it is useful & doesn't cause too many misconceptions

The last MakingMolecules #Chemistry #ChemEd #ChemSky of the year, but what a post, an org chemist introducing rates of reaction with collision theory! The pool analogy is shaky/orientation is important than direction/frequency not numbers). It's a vital topic but find a physical chemist for details.

After 2 months of aromatic chem, here is something a little different (but not that different) & a #Chemistry #ChemSky #ChemEd summary on conjugate or 1,4- or Michael additions. To sound like a stuck record, it is aimed at UG with only the general mechanism & brief notes on regioselectivity. Enjoy.

The last nucleophilic aromatic substitution #Chemistry #ChemEd #ChemSky summary is a summary of the previous summaries. It shows 4 mechanisms of nucleophilic aromatic substitution including classic substitution, aryne intermediates, ionic & radical substitution of diazonium salts. Hope it helps.

With stunning originality & a certain amount of flare, I give you Nucleophilic Aromatic Substitution 3. A #ChemEd #Chemistry #ChemSky summary discussing substitution via aryne intermediates. It is pitched at #UG. More detail/references at www.makingmolecules.com/blog/benzyne Hope it is useful Enjoy

The second #ChemEd #Chemistry #ChemSky summary on nucleophilic aromatic substitution. This time it covers the formation & use of diazonium salts. The substitution mechanism is either ionic or radical depending on the nucleophile. Good(ish) with paracyclophane (honest)! Hope this is useful. Enjoy

After 3 #Chemistry #ChemSky #ChemEd summaries on electrophilic aromatic substitution, we move to the nucleophilic variant SNAr (surprise). Not as common (due to structural limitations), but equally useful. Next week, the same reaction but with diazonium salts. Hopefully no silly mistakes this time!

Anyone for a summary of a summary? After two weeks of #ChemEd #ChemSky #Chemistry summaries on electrophilic aromatic substitution here, by popular demand, is one chart that covers just the basics. Enjoy.

More electrophilic aromatic substitution. Last week was the general reaction, today covers (de)activation & directing effects. It is a #UG simplification so no discussion of inductive effect vs hyperconjugation etc (or the transannular effect). Enjoy #ChemEd #Chemistry #ChemSky

Here's a #ChemEd #Chemistry #ChemSky summary of electrophilic aromatic substitution. As an ex-[2.2]paracyclophane chemist, this is a reaction dear to my heart. Here is just the basic mechanism aimed at UG (the mechanisms for electrophile activation are www.makingmolecules.com/blog/electro...). Enjoy

These #ChemEd #Chemistry #ChemSky summaries target early UG & the basics. Except when they don't. Here is a follow-up to anti-Markovnikov addition summary & a look at asymmetric hydroboration. It's still a summary. Only substrate control & pinene reagents. www.makingmolecules.com/blog/asymhyd...

No MakingMolecules #ChemEd summary today as NZ_Molecules is in Singapore with the wonderful folk at Gerstel (& only being a tiny bit jealous of their kit). I feel a summary of sensory directed analysis coming at some point as it is simply fascinating (& a powerful technique to help at work).

A #ChemEd #Chemistry #ChemSky summary of anti-Markovnikov addition to alkenes using radical hydrobromination or hydroboration/oxidation. It's classic UG material introducing regioselectivity/stabilising intermediates. It's a simplification, more at www.makingmolecules.com/blog/antimar...

No new #ChemEd #Chemistry #ChemSky summary today, just an attempt to summarise the alkene chemistry that has been covered in the last couple of infographics. It also acts as a spoiler for next week's look at anti-Markovnikov addition. Hopefully it still has some use.

A #ChemEd #Chemistry #ChemSky intro to the frontier molecular orbital view of electrophilic addition to alkenes. It is a companion to the last one (bsky.app/profile/maki...). It is an oversimplification but useful at #UG level (I hope). It shows the limitations of curly arrow mechanisms. Enjoy.

The 1st in a series of #ChemEd #Chemistry #ChemSky summaries on the reactions of alkenes. I'm starting with nucleophilic alkenes & the common UG reactions of the addition of HX, Br2, epoxidation etc. It's a bit crowded but hopefully it is useful. More details & reactions over the coming weeks.

A #ChemEd #Chemistry #ChemSky summary of acyl substitution. There is one mechanism repeated multiple times (with variations). It is addition & elimination. Acylation is possibly the most important reaction (along with proton transfer) for non-chemists taking chemistry. Hope this is useful. Enjoy.

More nucleophilic addition to aldehydes/ketones, this #ChemEd #Chemistry #ChemSky summary covers condensation & the formation/hydrolysis of acetals, imines & enamines. The mechanism is the same each time, but understanding why they deliver different products is important. Enjoy

A #ChemEd #Chemistry #ChemSky intro to models for explaining diastereoselectivity of nuc addition to C=O with an α stereocentre. It is a huge simplification. A tease for a fascinating subject. Other models exist but these are the ones often found at UG. Enjoy www.makingmolecules.com/blog/diaster...

This #ChemEd #Chemistry #ChemSky summary is an intro to nucleophilic addition to aldehydes/ketones. It's the 1st of many as I think carbonyl addition is far more useful than the traditional Sn1/Sn2 approach for teaching the basics (& more examples in biology). Hopefully it's useful. Enjoy.

There haven’t been any updates to MakingMolecules, as I was preparing a workshop on #SciCommun for MESA www.linkedin.com/company/macd... These slides (alt text for an explanation) give a flavour of the day. It was a fun day with a great bunch of scientists. MakingMolecules will return soon(ish).

It has become tradition for MakingMolecules to post a chemistry-related celebration of Matariki & the Māori New Year. This year I've added Puanga (Rigel) as it is more visible in the Manawatū. By luck, I have celebrated the 200 anniversary of benzene as well! www.chemistryworld.com/opinion/benz...

The previous #ChemEd #Chemistry #ChemSky summaries provided the background to org rcts (except the acid/base 1 which is THE most important org rct). Here are curly arrows, the last thing I need before starting reactions! It's a summary, more details elsewhere www.makingmolecules.com/blog/curlyar...

A #ChemEd #Chemistry #ChemSky summary on my favourite subject (after dairy chem of course), chirality. I love that a small change (reflection) makes a big difference. Students seem to hate chirality so here is a simple intro (more stereochem: www.makingmolecules.com/blog/tpyjoy3...)

Following the pKa scales, here is a #ChemEd #Chemistry #ChemSky intro to predicting relative acidity based on stability of the conjugate base. It's a simple #UG look at a complex subject. Far too simple in retrospect. Here is a blog (www.makingmolecules.com/blog/predict...) that gives more context.

The pKa of some org mols in MeCN. Like the earlier scales (H2O bsky.app/profile/maki... & DMSO bsky.app/profile/maki...), the data isn't mine (refs on sheet). This is an attempt to visualize the data differently. Some will like it, some won't. More #ChemEd #Chemistry summaries next week. Enjoy

Occasionally, I take #ChemEd #ChemSky requests & after the pKa scale in H2O, I was asked for DMSO & MeCN versions. Here it is for DMSO. As before, it's nothing new. Values are taken from Reich/Bordwell (ref at bottom of scale) & I've just tried to make them more visual. I like pictures not tables.

Re-inventing the wheel. Instead of a #ChemEd #Chemistry #ChemSky summary here is my version of a pKa (in H2O) scale. Values are taken from the wonderful Evans/Ripin & Hans Reich resources. If you want a table, I recommend these. This was an attempt at a more visual representation of the data Enjoy

The last 2 summaries looked at equilibria in preparation for this #ChemEd #Chemistry #ChemSky summary on acids/bases. Protonation (hydronation for the pedantic) & proton (does anyone call H+ a hydron?) transfers are probably the most important reaction in org chem. Enjoy this intro (more to come)

Seems I missed world frog day (bsky.app/profile/comp...) but here are some random posters I made when I was learning to use Affinity Designer. More than a little inspired by the records/designers I like, such as the Designers Republic ... there are lots more but they're all a little rubbish

The follow up to last week's #ChemEd #Chemistry #ChemSky summary on equilibria, this one looks at Le Chatelier's Principle & outlines the effect of common stresses on equilibria. Inspired either by Roy Lichtenstein or Damien Hirst, there are lots of dots (it's a joke ... Lichtenstein not Hirst)

From the vault, a #ChemEd #Chemistry #ChemSky summary on equilibria. It is an #UG intro not a detailed explanation. I say this whenever I cover phys org chem as I invariably find that I have over simplified or gone wrong & phys chemists love highlighting mistakes (mostly nicely but occasionally not)

The follow up to last week's #ChemEd #Chemistry #ChemSky summary (bsky.app/profile/maki...) on Diels-Alder-like reactions is below: It has more explanation & examples but is still only an intro. It still has a mistake in the hDA rct that I can't correct as I'm currently without ChemDraw Enjoy

Miracles happen, a new #Chemistry #ChemSky #ChemEd summary on variants of the Diels-Alder reaction. As always, it isn't a deep dive, I just wanted to show that the DA rct is really useful. I mention catalysis but there will be more detail in the wordy version next week. Hope it is useful & enjoy.

More stereochemical descriptors. This time a #Chemistry #ChemEd #ChemSky summary for naming planar chirality (as I love cyclophanes). To confuse the unwary, there are two conventions for metallocenes that give different answers (another reason to love cyclophanes instead). I hope this is useful

A niche #Chemistry #ChemSky #ChemEd summary, assigning stereochemical descriptors to axial & equatorial chirality. I know some argue these phrases are meaningless, but they're terms used by synthetic chemists. I know others just hate stereochemistry (you weirdos)! Hope it is useful (& corrected)

Fun with ChemDraw and Apple's Keynote (or a bit of a breather from 1 page summaries). Here is an attempt to show ring flipping with simple apps. As always, I hope this us useful for #ChemEd or #Chemistry #ChemSky ... having problems uploading the animated gif

Following alkyl conformations comes a #ChemEd #Chemistry #ChemSky summary on cyclohexane conformations. A popular topic at UG. Cyclohexane is boring (joke?) but rings with 6 sp3 hybridized atoms are interesting & this conformation can be used to predict the stereoselectivity of reactions. Enjoy.

#UG #ChemEd #Chemistry #ChemSky simple intro to conformations. No anomeric effect or electronics. The definitions of torsional/eclipsing strain (atoms 3 bonds apart) & steric strain (atoms >4 bonds apart) need clarification/inclusion/improvement. But still hopefully useful? Enjoy.

After a relaxing summer break, here are 3 versions of an old #ChemEd #Chemistry #ChemSky (from 2022) summary. The simplest is perhaps more suitable for high school (6th form in my own timeline & point of origin) while the others touch on atropisomerism so are suitable for UG. Hopefully useful? Enjoy

From May 22, a #ChemEd #Chemistry #ChemSky summary of assigning stereochemical descriptors. It's a skill (you could argue that it's not a useful skill thanks to apps like ChemDraw), I'd disagree. More details at www.makingmolecules.com/blog/7d9hspx... Hopefully, this was the corrected version ...

1st summary (from 2022) on every UGs favourite topic, stereochemistry. This #ChemEd #Chemistry #ChemSky intro avoids point groups/symmetry elements. Let the argument begin about the use of stereocentre to describe the carbon of an alkene. Happy to correct if there is a better term. Enjoy 🫤

Question for #Chemistry #ChatChemistry #iTeachChemistry I spent 25 yrs teaching org chemistry to 18+. Did a little outreach but always 16+. Now need Food Science practical projects for younger students 8-10. Should be simple/no specialist equipment/supplies. Does anyone have any favourites? Thanks

Another old #ChemEd #Chemistry #ChemSky 1 pg summary. It continues last week's non-covalent interactions & looks at boiling points & solubility/miscibility. It was aimed at 1st year non-chemists (most of my old students). But it reminds them that these properties are on a scale. Enjoy.

An old #ChemEd #Chemistry #ChemSky summary of non-covalent interactions. This was aimed at UG chemists not experts. It is a foundation. It avoids the intricacies of this topic (I love Schreiner's work on dispersion forces & have avoided discussing inductive effect of alkyl grps vs hyperconjugation)