Master Organic Chemistry LLC, 1831 12th Avenue South, #171, Nashville TN, USA 37203, © Copyright 2020, Master Organic Chemistry, Clemmensen Reduction of Ketones/Aldehydes to Alkanes. Clemmensen reduction is an organic reaction which leads to the formation of alkanes by reduction of aldehydes or ketones in presence of acid and with amalgamated zinc. Your email address will not be published. My org chem professor told me that clemmensen reduction of 1,3 dicarbonyl compounds gives a differently rearranged compound. Sign up here for about 30 cents/ day! Notify me via e-mail if anyone answers my comment. Description: Addition of zinc amalgam, Zn(Hg) and acid to a ketone results in an alkane. The substrate must be stable to strong acid. Copyright Online Organic Chemistry TutorSEO Services IT. There are two proposed mechanisms i.e. Clemmensen reduction is an organic reaction which leads to the formation of alkanes by reduction of aldehydes or ketones in presence of acid and with amalgamated zinc. Organic compounds are found all around us and form the essential substances used in daily life. It should have been 5,5-dimethyl-1,3-cyclohexanedione, 2,4,4-trimethyl cyclopentanone and 3-methyl-2-butanone. Like 3,3-dimethyl-1,5-cyclohexanedione, gives 1,3,3-trimethyl-cyclopentanone (less membered ring). I’m still in high school so I have no idea about the Dowd-Beckwith expansion reaction, however the Wikipedia page did throw some light on it. That is seriously funky. Clemmensen Reduction The Clemmensen Reduction allows the deoxygenation of aldehydes or ketones, to produce the corresponding hydrocarbon. This is called the Clemmensen reduction. The Danish chemist discovered this reaction named Erik Christian Clemmensen. On an Orgo 2 HW question we had to propose the synthesis of 1-bromo-3-propylbenzene. Could you explain how to approach that? About Clemmensen Reduction The reduction of carbonyl groups of aldehydes and ketones to methylene groups with amalgamated zinc and concentrated hydrochloric acid is known as Clemmensen reduction. The substrate should not be acid sensitive, if the substrate is acid sensitive then reduction is carried out by Wolff-Kishner reduction. I wonder if it’s generating a ketyl radical and then going through a cyclopropane, much like some versions of the Dowd-Beckwith rearrangement? Clemmensen’s reduction reaction is used to reduce carbonyl compounds to simple hydrocarbons. This page seems to offer an explanation, stating 1,3 dicarbonyls form ring contraction products via cyclopropanediols, trapped as acetates: I still haven’t fully understood it though. The Danish chemist discovered this reaction named Erik Christian Clemmensen. And 2,4-pentanedione gives 2-methyl-3-butanone. Your email address will not be published. This page is available to MOC Members only. What kept throwing me off was what order to put them in. It’s tricky!–Beckwith_ring-expansion_reaction. Required fields are marked *. Thanks so much for your help, this is a great site and is extremely useful! The reaction proceeds via carbanion intermediate. The Clemmensen Reduction is complementary to the Wolff-Kishner Reduction, which is run under strongly basic conditions. Also, in my previous comment I seem to have gotten the IUPAC names wrong. I honestly have no idea. Could you explain to me the mechanism of these reactions and suggest ways to write the product for any such dicarbonyl clemmensen reduction? carbanionic mechanism where the attack of Zn is involved and carbenoid mechanism where Zn act as a surface to perform reaction and it is a radical process. This site uses Akismet to reduce spam. However I think that shouldn’t be happening, since we aren’t using a alkyl halide side chain or AlBN. This is called the Clemmensen reduction. Learn how your comment data is processed. The mechanism of action is not exactly clear. This was a multiple choice question, so we had to figure out the order of using the clemmensen reduction, bromination of arenes, and friedel crafts. 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Email: Phone / Whatsapp : +91-9878492406 Skype ID: onlineorganicchemistry. Save my name, email, and website in this browser for the next time I comment. Clemmensen Reduction of Ketones/Aldehydes to Alkanes – Master Organic Chemistry Clemmensen Reduction of Ketones/Aldehydes to Alkanes Description: Addition of zinc amalgam, Zn (Hg) and acid to a ketone results in an alkane.


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