Comments on: Reagent Friday: TsCl (p-toluenesulfonyl chloride) and MsCl (methanesulfonyl chloride) https://www.masterorganicchemistry.com/2011/06/24/reagent-friday-tscl-p-toluenesulfonyl-chloride-and-mscl-methanesulfonyl-chloride/ Tue, 13 Jun 2023 15:16:51 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2011/06/24/reagent-friday-tscl-p-toluenesulfonyl-chloride-and-mscl-methanesulfonyl-chloride/#comment-658283 Tue, 13 Jun 2023 15:16:51 +0000 https://www.masterorganicchemistry.com/?p=1658#comment-658283 In reply to Bhavya Bansal.

When -OH is converted to -OTs, the bond that forms is O-S (O-SO2C6H5CH3) and the bond that breaks is O-H.

No bonds to carbon are formed or broken.

Therefore the stereochemistry of the C-O bond is unchanged.

]]>
By: Bhavya Bansal https://www.masterorganicchemistry.com/2011/06/24/reagent-friday-tscl-p-toluenesulfonyl-chloride-and-mscl-methanesulfonyl-chloride/#comment-658279 Tue, 13 Jun 2023 14:26:50 +0000 https://www.masterorganicchemistry.com/?p=1658#comment-658279 -Ts will be substituted on oxygen by SN1 or SN2 mechanism? ’cause there’s a question in which stereo of the molecule has been specified

]]>
By: Swarnabh https://www.masterorganicchemistry.com/2011/06/24/reagent-friday-tscl-p-toluenesulfonyl-chloride-and-mscl-methanesulfonyl-chloride/#comment-630841 Mon, 20 Jun 2022 19:54:59 +0000 https://www.masterorganicchemistry.com/?p=1658#comment-630841 So I’m preparing for one of the toughest entrance exams in the world and this site is legit making me dream of scoring full in Chemistry. Thanks a ton, Mr. James

]]>
By: Cheap Molecule Could Lower the Cost of Batteries – Chembites https://www.masterorganicchemistry.com/2011/06/24/reagent-friday-tscl-p-toluenesulfonyl-chloride-and-mscl-methanesulfonyl-chloride/#comment-619433 Sat, 29 Jan 2022 22:28:15 +0000 https://www.masterorganicchemistry.com/?p=1658#comment-619433 […] tanks of a redox flow battery. To make the molecule more soluble the authors reacted DAAQ with a sulfonyl chloride to produce a sulfonamidic acid with a negatively charged oxygen to increase the solubility in an […]

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2011/06/24/reagent-friday-tscl-p-toluenesulfonyl-chloride-and-mscl-methanesulfonyl-chloride/#comment-606376 Thu, 07 Oct 2021 14:44:37 +0000 https://www.masterorganicchemistry.com/?p=1658#comment-606376 In reply to Ghuj.

In practice, you will obtain a mixture that will require separation, and thus attempting to do so is impractical.
It is possible to selectively protect a primary alcohol through use of the extremely bulky triphenylmethyl (“trityl”) group.

]]>
By: Ghuj https://www.masterorganicchemistry.com/2011/06/24/reagent-friday-tscl-p-toluenesulfonyl-chloride-and-mscl-methanesulfonyl-chloride/#comment-606363 Thu, 07 Oct 2021 07:34:38 +0000 https://www.masterorganicchemistry.com/?p=1658#comment-606363 If you have a diol with secondary and primary alcohol on the same molecule, which you react with 1 equivalent of tosyl chloride, which alcohol will be converted to the tosylate?

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2011/06/24/reagent-friday-tscl-p-toluenesulfonyl-chloride-and-mscl-methanesulfonyl-chloride/#comment-585362 Fri, 25 Sep 2020 15:31:09 +0000 https://www.masterorganicchemistry.com/?p=1658#comment-585362 In reply to Chirag.

HCl will form. In some cases, particularly with benzylic or tertiary alcohols, the O will then be protonated, resulting in an even better leaving group. Through either ionization (SN1 pathway) or direct displacement, substitution of OTs for Cl can then occur. The result is that alkyl chlorides are obtained, sometimes with scrambling of stereochemistry due to the SN1 pathway. To prevent this, 1 equivalent of base is used.
Related to this: https://pubs.acs.org/doi/abs/10.1021/jo00829a084

]]>
By: Chirag https://www.masterorganicchemistry.com/2011/06/24/reagent-friday-tscl-p-toluenesulfonyl-chloride-and-mscl-methanesulfonyl-chloride/#comment-585323 Thu, 24 Sep 2020 11:51:28 +0000 https://www.masterorganicchemistry.com/?p=1658#comment-585323 What is we don’t use pyridine? Will it still replace OH to OTs?

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2011/06/24/reagent-friday-tscl-p-toluenesulfonyl-chloride-and-mscl-methanesulfonyl-chloride/#comment-564426 Wed, 18 Sep 2019 20:00:08 +0000 https://www.masterorganicchemistry.com/?p=1658#comment-564426 In reply to Sam.

Because strong acid creates R-OH2+ , which is itself a strong acid. What if you wanted to use as your nucleophile the acetylide ion RCC (-) ? That’s a useful way of making a new carbon-carbon bond, right? Well, the acetylide ion is very basic. If acid is present, then the acetylide ion will just be protonated to give the alkyne, ,RCCH. No reaction.
So, in short, one good reason is that a leaving group like OTs or OMs is more compatible with strongly basic nucleophiles. I discuss this more in this post: https://www.masterorganicchemistry.com/2015/03/10/tosylates-and-mesylates/

]]>
By: James Ashenhurst https://www.masterorganicchemistry.com/2011/06/24/reagent-friday-tscl-p-toluenesulfonyl-chloride-and-mscl-methanesulfonyl-chloride/#comment-564425 Wed, 18 Sep 2019 19:56:41 +0000 https://www.masterorganicchemistry.com/?p=1658#comment-564425 In reply to daya.

Tertiary alcohols may be converted to tosylates and mesylates, yes.

]]>