On an Orgo 2 HW question we had to propose the synthesis of 1-bromo-3-propylbenzene. This page seems to offer an explanation, stating 1,3 dicarbonyls form ring contraction products via cyclopropanediols, trapped as acetates: http://bit.ly/1CI3nhj I still haven’t fully understood it though. Learn how your comment data is processed. There are two proposed mechanisms i.e. Required fields are marked *. Thanks so much for your help, this is a great site and is extremely useful! This site uses Akismet to reduce spam. Your email address will not be published. The reaction proceeds via carbanion intermediate. 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. 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). That is seriously funky. Copyright Online Organic Chemistry TutorSEO Services IT. Save my name, email, and website in this browser for the next time I comment. This is called the Clemmensen reduction. http://en.wikipedia.org/wiki/Dowd–Beckwith_ring-expansion_reaction. Clemmensen Reduction The Clemmensen Reduction allows the deoxygenation of aldehydes or ketones, to produce the corresponding hydrocarbon. My org chem professor told me that clemmensen reduction of 1,3 dicarbonyl compounds gives a differently rearranged compound. 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. 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This is called the Clemmensen reduction. Organic compounds are found all around us and form the essential substances used in daily life. The Danish chemist discovered this reaction named Erik Christian Clemmensen. The mechanism of action is not exactly clear. I wonder if it’s generating a ketyl radical and then going through a cyclopropane, much like some versions of the Dowd-Beckwith rearrangement? Could you explain to me the mechanism of these reactions and suggest ways to write the product for any such dicarbonyl clemmensen reduction? I honestly have no idea. 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. Clemmensen’s reduction reaction is used to reduce carbonyl compounds to simple hydrocarbons. Your email address will not be published. This page is available to MOC Members only. http://en.wikipedia.org/wiki/Dowd–Beckwith_ring-expansion_reaction. 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. Description: Addition of zinc amalgam, Zn(Hg) and acid to a ketone results in an alkane. Could you explain how to approach that? It’s tricky! The Clemmensen Reduction is complementary to the Wolff-Kishner Reduction, which is run under strongly basic conditions. The Danish chemist discovered this reaction named Erik Christian Clemmensen. Notify me via e-mail if anyone answers my comment. However I think that shouldn’t be happening, since we aren’t using a alkyl halide side chain or AlBN. 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. Also, in my previous comment I seem to have gotten the IUPAC names wrong. 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. Email: email@example.com Phone / Whatsapp : +91-9878492406 Skype ID: onlineorganicchemistry. The substrate must be stable to strong acid. The substrate should not be acid sensitive, if the substrate is acid sensitive then reduction is carried out by Wolff-Kishner reduction. And 2,4-pentanedione gives 2-methyl-3-butanone. What kept throwing me off was what order to put them in. Sign up here for about 30 cents/ day! 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. 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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