Mechanic of isopulegon

[sosnas1994]

Can you look at my mechanic reaction of isopulegon from citronellol? I dont know how to write a proton transfer and i dont know the rest is correct

[Ramil]

 

Hope it helps

Good luck!

[chenbeier]

My question is what is CrO3Cl-, I know CrO2Cl2 and CrO42- or Cr2O7 2-.

Or is it a mixture of NaCl and CrO3?

[exchemist]

13 minutes ago, chenbeier said:

My question is what is CrO3Cl-, I know CrO2Cl2 and CrO42- or Cr2O7 2-.

Or is it a mixture of NaCl and CrO3?

Probably from this: https://en.wikipedia.org/wiki/Pyridinium_chlorochromate

Edited February 4 by exchemist

[chenbeier]

Ok this makes sense.

[Ramil]

Yes, CrO₃Cl^- is part of pyridinium chlorochromate (PCC) which is less reactive than other commonly used chromium-based reagents (such as Na₂Cr₂O7 with H₂SO₄) and is used in oxidation of primary alcohols to aldehydes (instead of to carboxylic acids)

Edited February 5 by Ramil

[exchemist]

6 hours ago, Ramil said:

Yes, CrO₃Cl^- is part of pyridinium chlorochromate (PCC) which is less reactive than other commonly used chromium-based reagents (such as Na₂Cr₂O7 with H₂SO₄) and is used in oxidation of primary alcohols to aldehydes (instead of to carboxylic acids)

Do you know when this reagent was introduced to the organic synthesis arsenal? I learned my organic synthesis back in the 1970s and I don't have a record of this one in my undergraduate book (ROC Norman) from that era, though it does of course have the dichromate method you mention. I see from Wiki this chlorochromate route was discovered "by accident" but there does not seem to be any information about when and how this came about. I wonder if it is more recent than my old books. 

[Ramil]

1 hour ago, exchemist said:

Do you know when this reagent was introduced to the organic synthesis arsenal? I learned my organic synthesis back in the 1970s and I don't have a record of this one in my undergraduate book (ROC Norman) from that era, though it does of course have the dichromate method you mention. I see from Wiki this chlorochromate route was discovered "by accident" but there does not seem to be any information about when and how this came about. I wonder if it is more recent than my old books. 

PCC reagent was first developed by Corey group in 1975. You can refer to this paper to see the details regarding its introduction. 

In regards to my background, I had to solve many Chemistry Olympiad problems back in high-school and I have seen this reagent overwhelmingly frequent. It seems it is used widely.

Hope it helps.

Edited February 5 by Ramil

[John Cuthber]

There are some reagents (Like LiAlH4) which get used a lot in exam questions and textbooks, but not so much in real life.

On paper they do the job.
In practice they tend to set your lab on fire, and chew through your budget.

Cr(VI) based oxidants are a bit too carcinogenic to be popular in industry.

(Yes, I know, there are exceptions.
The difference is that IiAlH4 might be your first choice in an exam, but it might not be in industry.

[exchemist]

2 hours ago, Ramil said:

PCC reagent was first developed by Corey group in 1975. You can refer to this paper to see the details regarding its introduction. 

In regards to my background, I had to solve many Chemistry Olympiad problems back in high-school and I have seen this reagent overwhelmingly frequent. It seems it is used widely.

Hope it helps.

It does, thanks. Looks as if my organic chemistry tutor might just have been becoming aware of this around the time I sat finals.🙂