Comments on: Synthesis Problems Involving Grignard Reagents https://www.masterorganicchemistry.com/2016/01/13/synthesis-using-grignard-reagents-1/ Tue, 02 Apr 2024 19:28:57 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2016/01/13/synthesis-using-grignard-reagents-1/#comment-689444 Tue, 02 Apr 2024 19:28:57 +0000 https://www.masterorganicchemistry.com/?p=9356#comment-689444 In reply to Grace Mbewe.

I think you’re describing a reaction where the alkene acts as a nucleophile on the carbocation electrophile, forming a cyclic five-membered ring with a new carbocation. There’s some examples in this article (go to the bottom) – https://www.masterorganicchemistry.com/2013/02/08/markovnikovs-rule-1/

]]> By: Grace Mbewe https://www.masterorganicchemistry.com/2016/01/13/synthesis-using-grignard-reagents-1/#comment-689439 Tue, 02 Apr 2024 18:45:56 +0000 https://www.masterorganicchemistry.com/?p=9356#comment-689439 Thanks alot you really help me but my question is having a skeletal structure like this one

/+\/\// having a carbonation how can one predict the nucleophile,electrophile and curved arrows to show the attack of the nucleophile on the electrophile

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2016/01/13/synthesis-using-grignard-reagents-1/#comment-654817 Thu, 11 May 2023 20:35:10 +0000 https://www.masterorganicchemistry.com/?p=9356#comment-654817 In reply to Ankita Somani.

No carbocation is formed. The new C-O pi bond forms at the same time as the C-O single bond breaks. This mechanism is known as “elimination” or sometimes 1,2-elimination.

No carbocation rearrangement occurs because there is no carbocation.

]]> By: Ankita Somani https://www.masterorganicchemistry.com/2016/01/13/synthesis-using-grignard-reagents-1/#comment-654790 Thu, 11 May 2023 13:22:46 +0000 https://www.masterorganicchemistry.com/?p=9356#comment-654790 hello sir.
in case of esters when the RO- group leaves, a carbocation is formed and thereafter oxygen donates it’s LP and we get a ketone. My question is if carbocation rearrangement will be possible?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2016/01/13/synthesis-using-grignard-reagents-1/#comment-626431 Mon, 02 May 2022 21:24:21 +0000 https://www.masterorganicchemistry.com/?p=9356#comment-626431 In reply to Sunnyway.

No, proton is too acidic for a Grignard. Will just deprotonate

]]> By: Sunnyway https://www.masterorganicchemistry.com/2016/01/13/synthesis-using-grignard-reagents-1/#comment-626349 Mon, 02 May 2022 05:12:59 +0000 https://www.masterorganicchemistry.com/?p=9356#comment-626349 Is -NHBoc compatible with grignard reagent? I am trying to make a grignard reagent bearing -NHBoc but turned unsuccessful. And I didn’t find similar examples from reaxys.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2016/01/13/synthesis-using-grignard-reagents-1/#comment-623605 Wed, 30 Mar 2022 01:52:47 +0000 https://www.masterorganicchemistry.com/?p=9356#comment-623605 In reply to Lynn.

Glad you find it helpful Lynn.

]]> By: Lynn https://www.masterorganicchemistry.com/2016/01/13/synthesis-using-grignard-reagents-1/#comment-623602 Wed, 30 Mar 2022 01:23:09 +0000 https://www.masterorganicchemistry.com/?p=9356#comment-623602 thank you so much for this, cheers!

]]> By: David Mucheru https://www.masterorganicchemistry.com/2016/01/13/synthesis-using-grignard-reagents-1/#comment-597324 Sat, 30 Jan 2021 12:32:13 +0000 https://www.masterorganicchemistry.com/?p=9356#comment-597324 Wow Really helpful especially in the retro synthesis products

]]> By: Tumwizere gerard https://www.masterorganicchemistry.com/2016/01/13/synthesis-using-grignard-reagents-1/#comment-586208 Fri, 16 Oct 2020 17:24:12 +0000 https://www.masterorganicchemistry.com/?p=9356#comment-586208 Thank you for that helpful post

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