Comments on: Exploring Resonance: Pi-Donation https://www.masterorganicchemistry.com/2011/12/15/exploring-resonance-pi-donation/ Thu, 07 Dec 2023 22:27:55 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: 7 Factors That Stabilize Positive Charge in Organic Chemistry | Straight A Mindset https://www.masterorganicchemistry.com/2011/12/15/exploring-resonance-pi-donation/#comment-679064 Thu, 07 Dec 2023 22:27:55 +0000 https://www.masterorganicchemistry.com/?p=3633#comment-679064 […] stability, which increases as the number of adjacent carbon atoms increases. Another example is π donation, where neighboring atoms with lone pairs can donate their electrons to electron-poor species such […]

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2011/12/15/exploring-resonance-pi-donation/#comment-645100 Thu, 29 Dec 2022 04:05:16 +0000 https://www.masterorganicchemistry.com/?p=3633#comment-645100 In reply to ashish.

Chlorines can also act as pi-donors, although they are much poorer pi-donors than nitrogen or oxygen.

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2011/12/15/exploring-resonance-pi-donation/#comment-637802 Mon, 12 Sep 2022 19:06:39 +0000 https://www.masterorganicchemistry.com/?p=3633#comment-637802 In reply to Ben Bowles.

I would say that pi-donation makes cationic polymerization a much more likely reaction pathway for vinyl ethers, although radical polymerization is not unprecedented. See here: https://pubs.acs.org/doi/10.1021/acs.macromol.6b00145

]]>
By: Ben Bowles https://www.masterorganicchemistry.com/2011/12/15/exploring-resonance-pi-donation/#comment-637657 Sat, 10 Sep 2022 23:46:45 +0000 https://www.masterorganicchemistry.com/?p=3633#comment-637657 Is pi-donation the reason why vinyl ethers do not undergo radical polymerisation, the resonance form prevents the initiating radical from reacting with the pi-electron?

]]>
By: ashish https://www.masterorganicchemistry.com/2011/12/15/exploring-resonance-pi-donation/#comment-581491 Tue, 23 Jun 2020 18:38:54 +0000 https://www.masterorganicchemistry.com/?p=3633#comment-581491 Vinyl chlorides, although less reactive, will also react with positive species at the end carbon (C-1)
shouldnt chlorines be the most electrophilic center

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2011/12/15/exploring-resonance-pi-donation/#comment-547776 Fri, 15 Feb 2019 22:50:37 +0000 https://www.masterorganicchemistry.com/?p=3633#comment-547776 In reply to Mudit.

You are right. Fixed it. Thank you.

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2011/12/15/exploring-resonance-pi-donation/#comment-547775 Fri, 15 Feb 2019 22:49:30 +0000 https://www.masterorganicchemistry.com/?p=3633#comment-547775 In reply to shivang.

That’s an excellent question. There are two ways by which atoms might have partial charge. The first, as you recall, is by examining electronegativities. The second is by analyzing resonance structures, as what we are doing here. It is only by analyzing the resonance structures (and the second-best resonance form, D) that helps us understand why there is a partial negative charge on the carbon.

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2011/12/15/exploring-resonance-pi-donation/#comment-547773 Fri, 15 Feb 2019 22:42:44 +0000 https://www.masterorganicchemistry.com/?p=3633#comment-547773 In reply to Camden.

Fixed. Thanks for catching that!

]]>
By: shivang https://www.masterorganicchemistry.com/2011/12/15/exploring-resonance-pi-donation/#comment-488666 Tue, 25 Oct 2016 14:05:26 +0000 https://www.masterorganicchemistry.com/?p=3633#comment-488666 hey James!!! if formal charges don`t always represent electron density then why deuterium attacked carbon?? since the formal charges don`t always represent electron density so electron density should be higher on oxygen…….

]]>
By: Camden https://www.masterorganicchemistry.com/2011/12/15/exploring-resonance-pi-donation/#comment-445381 Mon, 25 Jan 2016 04:59:58 +0000 https://www.masterorganicchemistry.com/?p=3633#comment-445381 “It reacts with readily with D+” in the figure on deuterating an enol. Get rid of the first “with”.

]]>