Comments on: Common Mistakes with Carbonyls: Carboxylic Acids… Are Acids! https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/ Tue, 23 Jan 2024 20:06:54 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: Souvik Paul https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/#comment-647437 Mon, 06 Feb 2023 09:01:42 +0000 https://www.masterorganicchemistry.com/?p=1534#comment-647437 ... Making Alcohol from Grignard reagent]]> My confusion is now totally wiped out
😃…
Making Alcohol from Grignard reagent

]]> By: Ajay https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/#comment-582204 Sun, 12 Jul 2020 10:50:45 +0000 https://www.masterorganicchemistry.com/?p=1534#comment-582204 I was too confused while solving questions. This post made it wayy clear.
Thanks.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/#comment-561998 Wed, 28 Aug 2019 03:49:01 +0000 https://www.masterorganicchemistry.com/?p=1534#comment-561998 In reply to Ajax.

Generally not, unless the acid chloride is extraordinarily hindered. C-H bonds don’t deprotonate as quickly as O-H bonds since 1) there has to be reorganization (rehybridization) of the bonds, and 2) the acidity of C-H is dependent on its alignment with the carbonyl.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/#comment-560172 Thu, 08 Aug 2019 17:33:27 +0000 https://www.masterorganicchemistry.com/?p=1534#comment-560172 In reply to Jim.

By “carboxylic acid chloride” it’s meant, “acid chloride” which in fact does not contain an acidic hydrogen. So protonation of the Grignard is not an issue here, although it would be with carboxylic acids.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/#comment-556076 Sat, 08 Jun 2019 04:24:49 +0000 https://www.masterorganicchemistry.com/?p=1534#comment-556076 In reply to Jesper.

Yes, exactly. The negatively charged oxygen is a strong pi donor and the carbonyl carbon is less electrophilic for this reason.

]]> By: Jesper https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/#comment-556022 Wed, 05 Jun 2019 23:35:48 +0000 https://www.masterorganicchemistry.com/?p=1534#comment-556022 A carboxylate actually has the charge delocalized between the two oxygens, This might explain why it isn’t keen on behaving like a carboxyl compound.

]]> By: NICKY KUMARI https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/#comment-554140 Thu, 25 Apr 2019 19:17:03 +0000 https://www.masterorganicchemistry.com/?p=1534#comment-554140 addition of nucleophile is not possible with HCOO- why? even it does not react with grignard reagent

]]> By: Sufyan https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/#comment-551806 Mon, 08 Apr 2019 03:29:45 +0000 https://www.masterorganicchemistry.com/?p=1534#comment-551806 Thanks

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/#comment-551265 Tue, 02 Apr 2019 04:06:34 +0000 https://www.masterorganicchemistry.com/?p=1534#comment-551265 In reply to Manoj.

The C-Br bond is much weaker than the C-O pi bond. Even if a C-Br bond did form, it would quickly be expelled to regenerate the carbonyl.

]]> By: Manoj https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/#comment-548236 Mon, 25 Feb 2019 11:19:14 +0000 https://www.masterorganicchemistry.com/?p=1534#comment-548236 Could you explain why HBr doesn’t add to a carbonyl in a nucleophilic addition??

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