Comments on: Hydrohalogenation of Alkynes https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/ Thu, 14 May 2026 17:30:25 +0000 hourly 1 https://wordpress.org/?v=6.9.4 By: James Ashenhurst https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-794261 Thu, 14 May 2026 17:30:25 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-794261 In reply to Nithin K.

There’s controversy about how likely the vinyl cation is in this mechanism. At the bottom of the post there is discussion about a termolecular mechanism.

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By: Nithin K https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-794179 Wed, 13 May 2026 10:52:21 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-794179 Isn’t a vinyl carbocation usually highly unstable for it to form appreciably?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-685970 Mon, 26 Feb 2024 16:39:44 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-685970 In reply to CHANDRU.

It is due to the electron-withdrawing nature of the halogens.

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By: CHANDRU https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-685967 Mon, 26 Feb 2024 16:28:04 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-685967 why halo alkenes are less reactive towards addition than corresponding alkenes ? is it some what regarding to the electron withdrawing effect of the halogen on the pi bond deecreasing its electron density ? similar to deactivating nature of halogen in aromatic rings ?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-679337 Sun, 10 Dec 2023 13:33:33 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-679337 In reply to Caroline Lyu.

Well, if the internal alkyne isn’t symmetrical, then there would be two constitutional isomers (alkenes). Each of those constitutional isomers would be present as a mixture of stereoisomers (E/Z) since these reactions are not very stereoselective.

So four, at least.

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By: Caroline Lyu https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-677333 Mon, 20 Nov 2023 23:46:47 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-677333 Hello,

What would the reaction look like for an internal alkyne, where there is equal substitution if the alkyne? How many constitutional isomers and products would be formed?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-642330 Mon, 14 Nov 2022 17:31:34 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-642330 In reply to Stanley.

The reaction uses stoichiometric (not catalytic) acid.

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By: Sabiu bawa https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-640081 Wed, 12 Oct 2022 12:57:24 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-640081 I have. Apriciation of this side. Alot

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By: Stanley https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-604269 Mon, 09 Aug 2021 11:52:31 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-604269 What catalyst is best for the hydrohalogenation process??

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By: Rohan Chowdhury https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-600151 Mon, 26 Apr 2021 07:11:02 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-600151 Can rearrangement take place in Hydrohalgenation of Alkynes like it happens in Alkenes.

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