Comments on: The Wolff-Kishner, Clemmensen, And Other Carbonyl Reductions https://www.masterorganicchemistry.com/2018/08/27/the-wolff-kishner-clemmensen-and-other-sidechain-reductions/ Thu, 08 Aug 2024 21:08:01 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: D.P. https://www.masterorganicchemistry.com/2018/08/27/the-wolff-kishner-clemmensen-and-other-sidechain-reductions/#comment-702535 Thu, 08 Aug 2024 21:08:01 +0000 https://www.masterorganicchemistry.com/?p=11813#comment-702535 Thanks a lot Sir! This website is saving me in my JEE Prep. Finally found a good website that has everything in a really good way.

]]> By: Achyuta https://www.masterorganicchemistry.com/2018/08/27/the-wolff-kishner-clemmensen-and-other-sidechain-reductions/#comment-696804 Sat, 15 Jun 2024 15:33:32 +0000 https://www.masterorganicchemistry.com/?p=11813#comment-696804 Sir, another way we have been taught to convert carbonyl to CH2 is by using red phosphorus(it’s a good reducing agent) along with hydroiodic acid. Can you please also include that reaction.

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2018/08/27/the-wolff-kishner-clemmensen-and-other-sidechain-reductions/#comment-680034 Mon, 18 Dec 2023 20:08:03 +0000 https://www.masterorganicchemistry.com/?p=11813#comment-680034 In reply to Tejas Johar.

Might be the aqueous acidic nature of the Clemmensen resulting in cleavage of the amide? Clemmensen not exactly known for its functional group tolerance.

]]> By: Tejas Johar https://www.masterorganicchemistry.com/2018/08/27/the-wolff-kishner-clemmensen-and-other-sidechain-reductions/#comment-679858 Sun, 17 Dec 2023 02:44:08 +0000 https://www.masterorganicchemistry.com/?p=11813#comment-679858 i came across a question where under clemmensen conditions an amide was changed into COOH in presence of ketone group but how is this possible as it is said that it selectively reduces carbonyl group and please tell its mech.
also please tell that if on beta carbon an alkyl group is present will it undergo reduction via elimination forming a double bond between alpha and beta?please tell the mechanism

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2018/08/27/the-wolff-kishner-clemmensen-and-other-sidechain-reductions/#comment-674813 Wed, 18 Oct 2023 19:35:25 +0000 https://www.masterorganicchemistry.com/?p=11813#comment-674813 In reply to thanong.

In general esters and other carboxylic acid derivatives are less reactive towards nucleophiles than ketones. Furthermore the OR group of the ester can act as a leaving group, so in the end what could just happen is nucleophilic acyl substitution at the ester.

]]> By: thanong https://www.masterorganicchemistry.com/2018/08/27/the-wolff-kishner-clemmensen-and-other-sidechain-reductions/#comment-674800 Wed, 18 Oct 2023 13:20:20 +0000 https://www.masterorganicchemistry.com/?p=11813#comment-674800 Why doesnt the carbonyl group in the ester not get reduced?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2018/08/27/the-wolff-kishner-clemmensen-and-other-sidechain-reductions/#comment-659288 Wed, 21 Jun 2023 20:04:06 +0000 https://www.masterorganicchemistry.com/?p=11813#comment-659288 In reply to Hemmema.

Under basic conditions the carboxylic acid is deprotonated to give a carboxylate, and these do not readily undergo addition to the C=O group (unlike ketones)

]]> By: Hemmema https://www.masterorganicchemistry.com/2018/08/27/the-wolff-kishner-clemmensen-and-other-sidechain-reductions/#comment-659268 Wed, 21 Jun 2023 16:14:09 +0000 https://www.masterorganicchemistry.com/?p=11813#comment-659268 Why wolf kishner do not reduce cooh ?

]]> By: James Ashenhurst https://www.masterorganicchemistry.com/2018/08/27/the-wolff-kishner-clemmensen-and-other-sidechain-reductions/#comment-657847 Fri, 09 Jun 2023 19:46:32 +0000 https://www.masterorganicchemistry.com/?p=11813#comment-657847 In reply to Lanre.

“Quizzes solution were dropped?” can you explain?

]]> By: Lanre https://www.masterorganicchemistry.com/2018/08/27/the-wolff-kishner-clemmensen-and-other-sidechain-reductions/#comment-657843 Fri, 09 Jun 2023 18:06:20 +0000 https://www.masterorganicchemistry.com/?p=11813#comment-657843 Please,I would appreciate it alot if the quizzes solution were dropped aswell,I feel it will go a long way in helping out alot of us.

]]>