Chemmunity Team

08 Apr 11:20

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Chemmunity Team 

"Sharpless reagents" usually refers to the set of reagents used in Sharpless asymmetric reactions, invented by K. Barry Sharpless. The two most famous ones are:

1. Sharpless Asymmetric Epoxidation

Used for: Epoxidizing allylic alcohols (alkenes with an -OH on the adjacent carbon)

Reagents:

Titanium(IV) isopropoxide (Ti(OiPr)â‚„)

(–)- or (+)-diethyl tartrate (DET) → gives the stereoselectivity!

tert-Butyl hydroperoxide (TBHP) → the oxidant

Product: Chiral epoxide with high enantioselectivity→ Which enantiomer you get depends on whether you use (+)-DET or (–)-DET

2. Sharpless Asymmetric Dihydroxylation

Used for: Converting alkenes to vicinal diols (2 adjacent OH groups), enantioselectively

Reagents:

OsOâ‚„ (osmium tetroxide, catalytic)

A chiral ligand like (DHQ)â‚‚PHAL or (DHQD)â‚‚PHAL

NMO (or another co-oxidant)

Product: A chiral diol with predictable stereochemistry→ Again, you choose the enantiomer using the right ligand

08 Apr 11:19

At this time we do not have any videos on this topic but I'll let the team know. For now here's information on these topics:

Oxone is the brand name for a triple salt:

2KHSO₅ · KHSO₄ · K₂SO₄

The key component here is potassium peroxymonosulfate (KHSOâ‚…), a powerful oxidizing agent.

What is it used for?

Epoxidation of alkenes

Oxidation of sulfides to sulfoxides/sulfones

Oxidation of alcohols (in some conditions)

Oxidative cleavage of alkenes to carbonyl compounds (less common)

07 Apr 11:42

Happy to hear you liked the video :) 

A common mistake students make during Hofmann elimination, aside from not choosing the correct β-carbon, is forgetting to form the quaternary ammonium salt before attempting the elimination step.

Here’s what happens:

Students sometimes jump straight into thinking it’s like an E2 reaction and try to eliminate directly from a regular amine (like a tertiary or secondary amine).

But Hofmann elimination requires converting the amine into a quaternary ammonium salt (usually using excess methyl iodide), followed by treatment with a strong base like silver oxide and water. Without this step, the elimination won't happen.

Other related mistakes include:

Using the wrong base — like hydroxide or an E2-style base instead of silver oxide and water.

Assuming Zaitsev product will form — Hofmann elimination is unique because it usually gives the least substituted (Hofmann) alkene, due to steric hindrance, not the most substituted like in E2 reactions.

hbr-peroxide-mechanism-.jpg

Here's an example of the worked out mechanism:

28 Mar 10:43

Thank you for bringing this to our attention, we will fix that. So sorry about that! 

Gustav Hestholm Yay! We are so happy to hear the video helped and that you're learning a lot. If there is any video you need help finding feel free to let us know. 

The video below walks you through all of this and more, Melissa lists what you should look for when ranking acids and determining the strongest acid and base. I highly recommend watching this lesson first then watching the Study with Us video for extra practice and common exam questions. 

31:08

Lesson: Acids and Bases

Timestamps:00:00 Acids and...

At timestamp 12:37 you'll see the intermediates are the ones that canceled out. This goes back to Chem 2 Kinetics where the intermediates are the ones that cancel out when finding the overall balanced reaction. Intermediates commonly formed in free radical halogenation are in the initiation step ( the 2 halogen radicals, 2 Cl• or 2 Br•), in the propagation step it's the alkyl radical formed (like methyl radical, CH₃•) and the regenerated halogen radical (Cl• or Br•). There are none in the termination step. 

In this video you'll also find intermediates shown at 29:35, this is specifically referring to energy diagrams and identifying the intermediate from the energy diagram. 

If you were looking for other nonradical reactions with examples of intermediates, we have a video that shows the intermediates for SN1 and E1 reactions it starts at timestamp 12:08 in the below video:

Lesson: Drawing Energy Diagrams for SN2, SN1, E2 and E1 Reactions

Does this answer your question?