Comments on: Ethers From Alkenes, Tertiary Alkyl Halides and Alkoxymercuration https://www.masterorganicchemistry.com/2014/11/07/synthesis-of-ethers-2-back-to-the-future/ Sat, 16 Sep 2023 03:25:59 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2014/11/07/synthesis-of-ethers-2-back-to-the-future/#comment-645962 Wed, 11 Jan 2023 19:07:16 +0000 https://www.masterorganicchemistry.com/?p=8611#comment-645962 In reply to andrew.

The mechanism of the final demercuration step is often not covered.

]]> By: AH https://www.masterorganicchemistry.com/2014/11/07/synthesis-of-ethers-2-back-to-the-future/#comment-643858 Tue, 06 Dec 2022 19:39:48 +0000 https://www.masterorganicchemistry.com/?p=8611#comment-643858 If I was asked what would occur with an alkene + ethanol in the presence of HCl, would the answer be nothing, since Cl isn’t a poorly nucleophillic counter-ion like you mentioned?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2014/11/07/synthesis-of-ethers-2-back-to-the-future/#comment-564446 Wed, 18 Sep 2019 21:06:01 +0000 https://www.masterorganicchemistry.com/?p=8611#comment-564446 In reply to Trevor Haas.

It would be a lot like oxymercuration: alkene would coordinate to the metal, and alcohol would attack the most substituted carbon. Except now you have an alkylpalladium species, and this will do beta-hydride elimination, resulting in a new double bond. So it will form an enol ether (if an alcohol is the nucleophile) or a ketone (if water is the nucleophile). For an example see the Wacker oxidation. https://www.organic-chemistry.org/namedreactions/wacker-tsuji-oxidation.shtm

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2014/11/07/synthesis-of-ethers-2-back-to-the-future/#comment-560788 Fri, 16 Aug 2019 18:21:29 +0000 https://www.masterorganicchemistry.com/?p=8611#comment-560788 In reply to Zaifful Gani.

Without seeing the specific example, it’s hard to say.

]]> By: Zaifful Gani https://www.masterorganicchemistry.com/2014/11/07/synthesis-of-ethers-2-back-to-the-future/#comment-560732 Fri, 16 Aug 2019 04:11:00 +0000 https://www.masterorganicchemistry.com/?p=8611#comment-560732 Is acid-catalyzed ether formation via alcohol reaction possible if what I have is a haloalkene/alkenyl halide? If yes, would it have the same mechanism as with your example in No. 2?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2014/11/07/synthesis-of-ethers-2-back-to-the-future/#comment-558692 Wed, 24 Jul 2019 01:40:34 +0000 https://www.masterorganicchemistry.com/?p=8611#comment-558692 In reply to Nea.

In theory: catalytic acid plus the appropriate alkene plus t-butyl alcohol.

]]> By: Nea https://www.masterorganicchemistry.com/2014/11/07/synthesis-of-ethers-2-back-to-the-future/#comment-558688 Wed, 24 Jul 2019 00:32:28 +0000 https://www.masterorganicchemistry.com/?p=8611#comment-558688 How would you make a di-tertbutyl ether from an alkene?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2014/11/07/synthesis-of-ethers-2-back-to-the-future/#comment-555278 Wed, 15 May 2019 02:16:57 +0000 https://www.masterorganicchemistry.com/?p=8611#comment-555278 In reply to giuseppe.

One way would be to start with cyclohexene, add Hg(OAc)2 and then cyclohexanol, followed by NaBH4 to do the demercuration. That would be one of the cleanest ways given the tools that you have.

]]> By: giuseppe https://www.masterorganicchemistry.com/2014/11/07/synthesis-of-ethers-2-back-to-the-future/#comment-526308 Thu, 11 Jan 2018 19:06:42 +0000 https://www.masterorganicchemistry.com/?p=8611#comment-526308 Hello,

How would you make dicyclohexyl ether?

Thanks

]]> By: andrew https://www.masterorganicchemistry.com/2014/11/07/synthesis-of-ethers-2-back-to-the-future/#comment-518425 Sat, 19 Aug 2017 04:53:53 +0000 https://www.masterorganicchemistry.com/?p=8611#comment-518425 Why do you say that oxymercuration is not a mechanism typically covered? UCLA teaches it in first quarter of organic chemistry and it was used as a vital reaction in many tough synthesis problems

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