Comments on: Demystifying The Mechanisms of Alcohol Oxidations https://www.masterorganicchemistry.com/2015/05/21/demystifying-alcohol-oxidations/ Sat, 05 Aug 2023 11:26:36 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: Yves de Montaudouin https://www.masterorganicchemistry.com/2015/05/21/demystifying-alcohol-oxidations/#comment-580429 Fri, 22 May 2020 22:55:40 +0000 https://www.masterorganicchemistry.com/?p=8939#comment-580429 Why do some reactant like Collins reagent stop their oxidation at the aldehyde level?
Is it just the absence of water?

]]> By: Yves de Montaudouin https://www.masterorganicchemistry.com/2015/05/21/demystifying-alcohol-oxidations/#comment-580425 Fri, 22 May 2020 20:32:05 +0000 https://www.masterorganicchemistry.com/?p=8939#comment-580425 Question:
If the hydrate happens BEFORE the actual attachment of the leaving group, why do we have different outcome with different leaving group?

]]> By: Yves de Montaudouin https://www.masterorganicchemistry.com/2015/05/21/demystifying-alcohol-oxidations/#comment-580423 Fri, 22 May 2020 20:19:31 +0000 https://www.masterorganicchemistry.com/?p=8939#comment-580423 Paragraph 2:
“2. Oxidants Are Essentially Just Fancy Reagents For Attaching Good “Leaving Groups” Directly To Oxygen”

Just fabulous

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/05/21/demystifying-alcohol-oxidations/#comment-550243 Mon, 18 Mar 2019 21:50:21 +0000 https://www.masterorganicchemistry.com/?p=8939#comment-550243 In reply to Mudit.

Yes – thank you, finally fixed!

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/05/21/demystifying-alcohol-oxidations/#comment-550242 Mon, 18 Mar 2019 21:49:57 +0000 https://www.masterorganicchemistry.com/?p=8939#comment-550242 In reply to Mateus.

Good luck. It’s complicated. Start with March’s advanced organic chemistry and dig in there.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/05/21/demystifying-alcohol-oxidations/#comment-550241 Mon, 18 Mar 2019 21:49:36 +0000 https://www.masterorganicchemistry.com/?p=8939#comment-550241 In reply to Carlos Klinger.

Not without breaking a C-C bond somehow.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2015/05/21/demystifying-alcohol-oxidations/#comment-550240 Mon, 18 Mar 2019 21:49:13 +0000 https://www.masterorganicchemistry.com/?p=8939#comment-550240 In reply to Christian Blanco.

There are some reagents that will preferentially oxidize primary over secondary, and vice-versa. You usually don’t learn about such details in introductory organic, but an example of the first type (primary over secondary) is TEMPO, and an example of the second type is Bobbitt’s reagent (among others)
See this super useful handout. http://hwpi.harvard.edu/files/myers/files/6-oxidation.pdf

]]> By: Christian Blanco https://www.masterorganicchemistry.com/2015/05/21/demystifying-alcohol-oxidations/#comment-537877 Sat, 08 Sep 2018 13:22:55 +0000 https://www.masterorganicchemistry.com/?p=8939#comment-537877 Hi, will there be a major product if a molecule with both primary and secondary alcohol is oxidized? I mean, is there a preference for oxidizing primary or secondary?

]]> By: Sean https://www.masterorganicchemistry.com/2015/05/21/demystifying-alcohol-oxidations/#comment-533353 Sat, 02 Jun 2018 02:06:48 +0000 https://www.masterorganicchemistry.com/?p=8939#comment-533353 I was wondering if the prof could give a quick answer on NAD+ as a leaving group. Nicotinamide Adenine Dinucleotide acts as a leaving group in the same way? Probably a weak oxidant?

Thank you.

]]> By: Carlos Klinger https://www.masterorganicchemistry.com/2015/05/21/demystifying-alcohol-oxidations/#comment-531514 Wed, 25 Apr 2018 23:21:01 +0000 https://www.masterorganicchemistry.com/?p=8939#comment-531514 Hi!
I loved your site! You explain very well!
I have a doubt…
How can I convert secondary alcohols into aldehydes? it’s possible?

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