Comments on: Alkyne Halogenation: Bromination and Chlorination of Alkynes https://www.masterorganicchemistry.com/2013/05/29/alkyne-halogenation-bromination-chlorination/ Thu, 07 May 2026 00:06:59 +0000 hourly 1 https://wordpress.org/?v=6.9.4 By: James Ashenhurst https://www.masterorganicchemistry.com/2013/05/29/alkyne-halogenation-bromination-chlorination/#comment-779667 Thu, 06 Nov 2025 20:15:58 +0000 https://www.masterorganicchemistry.com/?p=7348#comment-779667 In reply to NF.

Yes, that’s also an issue, but due to the poorer overlap of 1st-row carbon 2p with the 3p (for chlorine) or 4p (for bromine) orbitals and the corresponding longer bond lengths it’s considerably less of an obstacle than with oxirene.

Alkynes are just generally less nucleophilic than alkenes.

]]> By: NF https://www.masterorganicchemistry.com/2013/05/29/alkyne-halogenation-bromination-chlorination/#comment-779665 Thu, 06 Nov 2025 19:48:39 +0000 https://www.masterorganicchemistry.com/?p=7348#comment-779665 Re: Note 3. Wouldn’t the bigger issue with halogenation of alkynes, and the bigger contributor to slow speeds, be the anti-aromatic character of the bridged ion? (Compare to oxirene.)

Is it possible the addition follows a more concerted but also more convoluted pathway to avoid an anti-aromatic intermediate?

]]> By: Banonya Ali https://www.masterorganicchemistry.com/2013/05/29/alkyne-halogenation-bromination-chlorination/#comment-770382 Sat, 06 Sep 2025 15:45:48 +0000 https://www.masterorganicchemistry.com/?p=7348#comment-770382 Synthesis of the first five alkynes from bromo ethane
Waiting for your reply
Thank you so much

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2013/05/29/alkyne-halogenation-bromination-chlorination/#comment-757901 Fri, 04 Jul 2025 13:56:44 +0000 https://www.masterorganicchemistry.com/?p=7348#comment-757901 In reply to Nipun Kulshrestha.

Very unselective

]]> By: Shubhankar https://www.masterorganicchemistry.com/2013/05/29/alkyne-halogenation-bromination-chlorination/#comment-757733 Thu, 03 Jul 2025 15:56:58 +0000 https://www.masterorganicchemistry.com/?p=7348#comment-757733 ]]> Thanks sir 👍

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2013/05/29/alkyne-halogenation-bromination-chlorination/#comment-757726 Thu, 03 Jul 2025 15:50:28 +0000 https://www.masterorganicchemistry.com/?p=7348#comment-757726 In reply to Shubhankar.

*anti* atomatic. One pi bond from the alkene, and another from a lone pair of the bromine.

For an example of a three-membered ring that has antiaromatic character, see oxirene:
https://en.wikipedia.org/wiki/Oxirene

]]> By: Shubhankar https://www.masterorganicchemistry.com/2013/05/29/alkyne-halogenation-bromination-chlorination/#comment-756865 Mon, 30 Jun 2025 08:43:49 +0000 https://www.masterorganicchemistry.com/?p=7348#comment-756865 One of three lone pairs of cl has contribution to it

]]> By: Shubhankar https://www.masterorganicchemistry.com/2013/05/29/alkyne-halogenation-bromination-chlorination/#comment-756863 Mon, 30 Jun 2025 08:41:43 +0000 https://www.masterorganicchemistry.com/?p=7348#comment-756863 Hi ,

Why in Note 2 you mentioned that the antiaromatic character of cyclic brominium ion of alkyne halogenation?
Is the 1 pie bond makes it aromatic ??
Kindly explain me sir

]]> By: Sawaira https://www.masterorganicchemistry.com/2013/05/29/alkyne-halogenation-bromination-chlorination/#comment-649194 Wed, 01 Mar 2023 11:06:06 +0000 https://www.masterorganicchemistry.com/?p=7348#comment-649194 Thank you

]]> By: Nipun Kulshrestha https://www.masterorganicchemistry.com/2013/05/29/alkyne-halogenation-bromination-chlorination/#comment-618167 Fri, 07 Jan 2022 04:07:55 +0000 https://www.masterorganicchemistry.com/?p=7348#comment-618167 But how is C2H6 an alkyne?

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