Comments on: Introduction to Oxidative Cleavage Reactions https://www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/ Mon, 15 Aug 2022 02:34:50 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: Naa https://www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/#comment-582451 Thu, 23 Jul 2020 01:25:34 +0000 https://www.masterorganicchemistry.com/?p=2567#comment-582451 This was very helpful.
It’s actually making organic chemistry much easier to comprehend.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/#comment-563890 Thu, 12 Sep 2019 21:08:42 +0000 https://www.masterorganicchemistry.com/?p=2567#comment-563890 In reply to prem.

It’s possible to treat an alkene with ozone (O3) and obtain alkenes from oxidative cleavage. The products will depend on the structure of the starting alkene as well as the choice of workup for ozonolysis.

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/#comment-563268 Thu, 05 Sep 2019 18:35:49 +0000 https://www.masterorganicchemistry.com/?p=2567#comment-563268 In reply to Richard.

Yes, ozone would cleave an unsaturated fatty acid. Assuming the C=C was disubstituted, then yes, you’d end up with one molecule being an aldehyde and the other being an aldehyde-acid. You are right!

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By: James Ashenhurst https://www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/#comment-560162 Thu, 08 Aug 2019 17:19:39 +0000 https://www.masterorganicchemistry.com/?p=2567#comment-560162 In reply to David.

For ozonolysis, steric factors are rarely a concern. Bigger factor is that greater substitution on the double bond leads to a more electron-rich alkene and then a faster reaction (cycloaddition).

For diols, I suppose it could be somewhat of a concern but we’re usually forming bonds between oxygen and Pb or I which do not form long bonds to start with and have ligands which are easy to displace. In my experience, not a big issue.

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By: David https://www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/#comment-559594 Sat, 03 Aug 2019 21:33:08 +0000 https://www.masterorganicchemistry.com/?p=2567#comment-559594 Concerning the different reagents that can be used, which ones are most impacted by the sterics of the substrate?

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By: prem https://www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/#comment-495873 Thu, 08 Dec 2016 02:51:35 +0000 https://www.masterorganicchemistry.com/?p=2567#comment-495873 In reply to Annie.

How can alkenes form aldehyde

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By: Richard https://www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/#comment-494091 Sat, 26 Nov 2016 17:40:23 +0000 https://www.masterorganicchemistry.com/?p=2567#comment-494091 Dear James,
Thanks for this
I was just wondering, if you added O3, Zn and acid to a unsaturated fatty acid, would you still cleave the C=C bond? And would the products be an aldehyde and a molecule with a carboxyl group at one end and an aldehyde group at the other?

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By: James https://www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/#comment-71680 Tue, 25 Feb 2014 16:08:30 +0000 https://www.masterorganicchemistry.com/?p=2567#comment-71680 In reply to Annie.

Well, there’s an aldehyde – so think backwards. The C=O of the aldehyde came from being part of an alkene. And the C-H of the aldehyde was also present in the alkene. If there’s 4 carbons total, then there must be 3 carbons attached to the aldehyde carbonyl, so there should be three extra carbons attached to the carbon of the alkene that becomes the aldehyde after oxidative cleavage.

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By: Annie https://www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/#comment-70558 Tue, 18 Feb 2014 23:14:00 +0000 https://www.masterorganicchemistry.com/?p=2567#comment-70558 I was wondering what alkenes can form an aldehyde with four carbons as a result of oxidative cleavage?

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By: james https://www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/#comment-2520 Tue, 06 Mar 2012 21:59:04 +0000 https://www.masterorganicchemistry.com/?p=2567#comment-2520 In reply to Julie.

Hi Julie, you can cite the site name and the URL if you wish. The post is just a summary of data you’d see in textbooks, although more focused on a specific issue.

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