Comments on: Cleavage Of Ethers With Acid https://www.masterorganicchemistry.com/2014/11/19/ether-cleavage/ Thu, 22 Jan 2026 21:06:50 +0000 hourly 1 https://wordpress.org/?v=6.9.4 By: James Ashenhurst https://www.masterorganicchemistry.com/2014/11/19/ether-cleavage/#comment-789169 Thu, 22 Jan 2026 21:06:50 +0000 https://www.masterorganicchemistry.com/?p=8631#comment-789169 In reply to Dr Harsha.

It depends on the structure of the ether. Ethers connected to tertiary carbon will fragment via SN1, and ethers connected to primary carbons will fragment via SN2. It’s the middle ground (secondary) where there will be a mixture of the two pathways.

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By: Dr Harsha https://www.masterorganicchemistry.com/2014/11/19/ether-cleavage/#comment-789082 Thu, 22 Jan 2026 03:50:59 +0000 https://www.masterorganicchemistry.com/?p=8631#comment-789082 Sir ether in the presence of concentrated HI and anhydrous HI, is there any change in mechanism sn1 or sn2? Please reply

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By: Uditi https://www.masterorganicchemistry.com/2014/11/19/ether-cleavage/#comment-653819 Mon, 01 May 2023 09:54:28 +0000 https://www.masterorganicchemistry.com/?p=8631#comment-653819 If there is a conjugated system ie, (CH3)2-C=CH-O-CH=CH2 how will we decide where should be carbocation, and how will double bond get affected?

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By: James Ashenhurst https://www.masterorganicchemistry.com/2014/11/19/ether-cleavage/#comment-648615 Tue, 21 Feb 2023 16:59:42 +0000 https://www.masterorganicchemistry.com/?p=8631#comment-648615 In reply to Chandru.

It is difficult to predict with unsymmetrical di-alkyl ethers. What often happens is that excess H-I is used such that both alkyl fragments are converted into alkyl iodides.

It is easier with aryl alkyl ethers, which will never result in cleavage of the aryl-O bond

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By: Chandru https://www.masterorganicchemistry.com/2014/11/19/ether-cleavage/#comment-648424 Sat, 18 Feb 2023 16:54:02 +0000 https://www.masterorganicchemistry.com/?p=8631#comment-648424 Sir can we consider the solvent in the case of bond breaking in unsymmetrical ethers???
To identify sn1 or sn2

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By: James Ashenhurst https://www.masterorganicchemistry.com/2014/11/19/ether-cleavage/#comment-606391 Thu, 07 Oct 2021 19:14:50 +0000 https://www.masterorganicchemistry.com/?p=8631#comment-606391 In reply to Anonymous.

Hard to predict from first principles without doing the experiment.
However, one way to know for sure is to use a large excess of HI, which will give you both isopropyl iodide and methyl iodide.

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By: Anonymous https://www.masterorganicchemistry.com/2014/11/19/ether-cleavage/#comment-606377 Thu, 07 Oct 2021 14:47:29 +0000 https://www.masterorganicchemistry.com/?p=8631#comment-606377 ]]> If we take isopropyl methyl ether with HI,then what would be the major product? Please tell๐Ÿ™

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By: Harshil Kakkad https://www.masterorganicchemistry.com/2014/11/19/ether-cleavage/#comment-605811 Sat, 25 Sep 2021 00:14:17 +0000 https://www.masterorganicchemistry.com/?p=8631#comment-605811 Phenol + Ch3I

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By: James Ashenhurst https://www.masterorganicchemistry.com/2014/11/19/ether-cleavage/#comment-603239 Wed, 07 Jul 2021 15:18:33 +0000 https://www.masterorganicchemistry.com/?p=8631#comment-603239 In reply to Ryn.

Correct.

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By: Ryn https://www.masterorganicchemistry.com/2014/11/19/ether-cleavage/#comment-603038 Thu, 01 Jul 2021 05:01:11 +0000 https://www.masterorganicchemistry.com/?p=8631#comment-603038 We shall obtain phenol and methyliodide if I’m not wrong.

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