Comments on: Addition-Elimination Mechanisms With Neutral Nucleophiles (Including Acid Catalysis) https://www.masterorganicchemistry.com/2010/05/21/carbonyl-elimination-mechanism/ Mon, 22 May 2023 20:34:30 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: James Ashenhurst https://www.masterorganicchemistry.com/2010/05/21/carbonyl-elimination-mechanism/#comment-645905 Wed, 11 Jan 2023 09:49:00 +0000 http://masterorganicchemistry.wordpress.com/?p=381#comment-645905 In reply to Jay.

Dimethyl carbonate is not an ester, it is a carbonate, which is a different functional group.

One of the key reactions of amines with carbonates is to install protective groups, such as the Boc group, and it is generally done under basic conditions (i.e. not just water, but water in the presence of a base such as sodium carbonate). Representative procedures can be found on this page:
https://www.organic-chemistry.org/protectivegroups/amino/boc-amino.htm

]]> By: Jay https://www.masterorganicchemistry.com/2010/05/21/carbonyl-elimination-mechanism/#comment-644910 Sun, 25 Dec 2022 14:18:28 +0000 http://masterorganicchemistry.wordpress.com/?p=381#comment-644910 When aliphatic primary amines react with esters, for example, butylene diamine with dimethyl carbonate, the reaction rate is quite slow, but when water is added, it become very quick. How to explain this phenomenon?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2010/05/21/carbonyl-elimination-mechanism/#comment-547718 Thu, 14 Feb 2019 22:24:11 +0000 http://masterorganicchemistry.wordpress.com/?p=381#comment-547718 In reply to OBear.

AcO(-) means acetyl: CH3C(O)O- , the conjugate base of acetic acid

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2010/05/21/carbonyl-elimination-mechanism/#comment-547717 Thu, 14 Feb 2019 22:23:37 +0000 http://masterorganicchemistry.wordpress.com/?p=381#comment-547717 In reply to Jonathan.

Yes – great example. The Cl3C(-) anion leaves via a [1,2] elimination reaction.

]]> By: Jonathan https://www.masterorganicchemistry.com/2010/05/21/carbonyl-elimination-mechanism/#comment-543221 Tue, 13 Nov 2018 18:38:56 +0000 http://masterorganicchemistry.wordpress.com/?p=381#comment-543221 Would the haloform reaction which involves nucleophilic attack by OH followed by displacement of a CBr3 group also count?

]]> By: OBear https://www.masterorganicchemistry.com/2010/05/21/carbonyl-elimination-mechanism/#comment-494853 Wed, 30 Nov 2016 20:32:00 +0000 http://masterorganicchemistry.wordpress.com/?p=381#comment-494853 “…(Halides, AcO(-),…”

What does AcO(-) mean?
Thanks!

]]> By: Common Mistakes with Carbonyls: Carboxylic Acids… Are Acids! https://www.masterorganicchemistry.com/2010/05/21/carbonyl-elimination-mechanism/#comment-879 Fri, 02 Sep 2011 18:52:38 +0000 http://masterorganicchemistry.wordpress.com/?p=381#comment-879 […] like HO- and RO- . The pattern becomes familiar quite quickly: 1,2 addition, followed by 1,2 elimination. Seeing this pattern, students get lulled into a false sense of security that carboxylic acids will […]

]]>