Comments on: Hydrohalogenation of Alkynes https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/ Mon, 26 Feb 2024 16:39:44 +0000 hourly 1 https://wordpress.org/?v=6.6.2 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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By: James Ashenhurst https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-597475 Tue, 02 Feb 2021 19:24:11 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-597475 In reply to Mal.

Alkenes will be more reactive toward HBr than alkynes. A molecule with both an alkene and an alkyne will react with HBr at the alkene. When an alkene is protonated, the resulting carbocation is sp2 hybridized (33% s character) . When an alkyne is protonated the resulting carbocation is sp hybridized (50% s character). The more s-character present in a carbocation, the harder it is to form (less stable) since the empty orbital will be closer to the nucleus.

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By: Mal https://www.masterorganicchemistry.com/2013/05/24/hydrohalogenation-of-alkynes/#comment-597463 Tue, 02 Feb 2021 07:38:53 +0000 https://www.masterorganicchemistry.com/?p=7329#comment-597463 I have questions. What happen if a molecule contain both double bond and triple bond? Do both will be reacted with HBr? And how if only 1 mol of HBr is used? I really confused because i thought maybe one of them will react since only one HBr molecule will react for one reactant molecule.

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