Comments on: Carbonyl Chemistry: Learn Six Mechanisms For the Price Of One https://www.masterorganicchemistry.com/2011/03/28/caarbonyl-chemistry-learn-six-mechanisms-for-the-price-of-one/ Wed, 21 Aug 2024 09:06:36 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: Venkatachalam.N https://www.masterorganicchemistry.com/2011/03/28/caarbonyl-chemistry-learn-six-mechanisms-for-the-price-of-one/#comment-703779 Wed, 21 Aug 2024 09:06:36 +0000 https://www.masterorganicchemistry.com/?p=1438#comment-703779 i need a pdf with all carboylic acid derivaitves
and list of all organic derivatives

]]> By: Milad https://www.masterorganicchemistry.com/2011/03/28/caarbonyl-chemistry-learn-six-mechanisms-for-the-price-of-one/#comment-682384 Sun, 14 Jan 2024 12:17:19 +0000 https://www.masterorganicchemistry.com/?p=1438#comment-682384 Hello, I’d like to know how could we tell which functional group in a molecule is more reactive than the other, in other words : on which functional group the reaction will take place ( like in the case of addition or protonation). I also have the same question but this time for atoms in the same functional group like for example which oxygen in an ester is more basic and thus would undergo protonation by an acid or in the case of the last reaction in this post ”Conversion of carboxylic acids to anhydrides” why was it the oxygen with the H that did the 1,2 addition and not the oxygen with the double bond ? it’s the same atom (O) and it has the same number of lone electron pairs (2). do you have a post or several posts that covers all of these questions ? If yes could you please provide the link(s) to them ?

]]> By: Dippin chachan(india) https://www.masterorganicchemistry.com/2011/03/28/caarbonyl-chemistry-learn-six-mechanisms-for-the-price-of-one/#comment-580186 Thu, 14 May 2020 05:07:25 +0000 https://www.masterorganicchemistry.com/?p=1438#comment-580186 The RDX step of acyl substitution-elimination reactions like all those above is the formation of tetrahedral intermidiate,so rate of reactions should almost depend on the energy of Transition state of this step and this Transition state only consists of formation of transition bond of nucleophile with carbonyl carbon and breaking of carbonyl oxygen pi bond.There is no role of the bond of the leaving group(LEAVING GROUP:the group which leaves at last) .Then why rate of acyl substitution depend on the tendency of leaving group to leave(eg. acyl chloride are most reactive and amides are least reactive).

]]> By: Jason H. https://www.masterorganicchemistry.com/2011/03/28/caarbonyl-chemistry-learn-six-mechanisms-for-the-price-of-one/#comment-530808 Wed, 11 Apr 2018 19:56:26 +0000 https://www.masterorganicchemistry.com/?p=1438#comment-530808 Great post as always!

In Klein’s text, he explains that protonation of the carbonyl O is not likely in the production of imines or enamines. So that threw me a bit off.

Secondly, in your mechanism for anhydride 1,2-addition, the arrow doesn’t make sense. (At least from my perspective)

Thanks!

]]> By: Ben https://www.masterorganicchemistry.com/2011/03/28/caarbonyl-chemistry-learn-six-mechanisms-for-the-price-of-one/#comment-522827 Thu, 09 Nov 2017 04:29:14 +0000 https://www.masterorganicchemistry.com/?p=1438#comment-522827 If it helps anybody, the mnemonic PAPER works for this mechanism; it’s not super specific, but IMO mnemonics are meant to help rejog your memory:

Protonate Carbonyl
Addition of Nucleophile
Proton Transfer
Eliminate H2O
Restore Carbonyl via Deprotonation

]]> By: Mukund https://www.masterorganicchemistry.com/2011/03/28/caarbonyl-chemistry-learn-six-mechanisms-for-the-price-of-one/#comment-447808 Fri, 19 Feb 2016 10:51:15 +0000 https://www.masterorganicchemistry.com/?p=1438#comment-447808 In reply to Ryan McCauslin.

If you read it again it says “which previously acted as a nucleophile”.
Electrophilic substances are either positively charged or have vacant orbitals which attract electrons(or they are attracted to electrons?).In this case proton transfer from oxygen doesn’t make it an electrophile.

]]> By: Mukund https://www.masterorganicchemistry.com/2011/03/28/caarbonyl-chemistry-learn-six-mechanisms-for-the-price-of-one/#comment-447802 Fri, 19 Feb 2016 10:32:24 +0000 https://www.masterorganicchemistry.com/?p=1438#comment-447802 Omg I can’t even express in words how useful this website is for my exam preparation.
THANK YOU. Really appreciate it:D

]]> By: Tom https://www.masterorganicchemistry.com/2011/03/28/caarbonyl-chemistry-learn-six-mechanisms-for-the-price-of-one/#comment-383383 Thu, 02 Apr 2015 11:07:44 +0000 https://www.masterorganicchemistry.com/?p=1438#comment-383383 Hi James,

I love this! Isn’t the anagram a bit misleading for the formation of imines? I get that you need to protonate the O at some point but surely as a 1st step it would inhibit the approach of the RNH2 (which would also presumably protonate before C=O)

Thanks, Tom

]]> By: Tara https://www.masterorganicchemistry.com/2011/03/28/caarbonyl-chemistry-learn-six-mechanisms-for-the-price-of-one/#comment-363609 Thu, 12 Feb 2015 05:01:57 +0000 https://www.masterorganicchemistry.com/?p=1438#comment-363609 Hi,
I have a huge orgo 2 exam in two weeks. I’m a little confused about the mechanisms. I’m always confused on what will be protonated/ deprotonated in the different mechanisms. I’m still waiting for that lightbulb to go off haha. My professor wants us to memorize the mechanisms, but I’d like to know exactly why all the steps in each mechanism happen the way they do. I really want to understand this better. Help =(

]]> By: James https://www.masterorganicchemistry.com/2011/03/28/caarbonyl-chemistry-learn-six-mechanisms-for-the-price-of-one/#comment-333975 Tue, 02 Dec 2014 14:15:27 +0000 https://www.masterorganicchemistry.com/?p=1438#comment-333975 In reply to Simwawa.

Shoot. You are correct. Thanks for the spot.

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