In general enols are unstable compounds and they are in an equilibrium with a more favourable carbonyl group. flashcard set{{course.flashcardSetCoun > 1 ? Try to draw the mechanism for these processes before you look at the answers. For a redox reaction their wouldn't be a double bond alternation, all you would see is C=O bond if it's getting oxidized or a C-OH bond if it's getting reduced. Tautomerism definition, the ability of certain organic compounds to react in isomeric structures that differ from each other in the position of a hydrogen atom and a double bond. My impression was that if you reduce the number of C-O bonds or increase the number of C-H bonds, you are reducing a molecule. I’m going to focus on aldehydes and ketones in this post, however, so I don’t overload it with the … Enolization & Keto-Enol Tautomerism Read More » After the revival of r/MCAT, this page will be utilized as a additional platform to serve the pre-meds with their help on MCAT. Thus, tautomerization is an actual vigorous chemical reaction that can occur. Note that the enolate ion in the example is similar to the neutral molecule below. Keto-Enol Tautomerization vs. Enolate Resonance OH Resonance Stabilized Enolate Anion Keto-Enol Tautomerization Keto form Enol Enolate Resonance H 3C O C Keto form α-hydrogen pK a = 18-20 H H H H 3C O C H H H Acid or Base H 3C O N Amide Resonance VERY IMPORTANT!!!!! 's' : ''}}. More information on the movement of molecules is provided in the accompanying lesson called Tautomerization vs. Resonance. - Definition & Examples, Introduction to Chemistry: Tutoring Solution, Measurement and Problem Solving: Tutoring Solution, Experimental Laboratory Chemistry: Tutoring Solution, Understanding Atomic Structure: Tutoring Solution, The Periodic Table of Elements: Tutoring Solution, The Representative Elements of the Periodic Table: Tutoring Solution, Phase Changes for Liquids and Solids: Tutoring Solution, Solutions in Chemistry: Tutoring Solution, Stoichiometry and Chemical Equations: Tutoring Solution, Acids, Bases and Reactions: Tutoring Solution, Thermodynamics in Chemistry: Tutoring Solution, Chemistry of Nucleic Acids - DNA and RNA: Tutoring Solution, Chemistry of DNA Replication: Tutoring Solution, Working Scholars® Bringing Tuition-Free College to the Community, Organization of electrons in resonance structures, Basic or acid conditions for tautomerization. Cookies help us deliver our Services. Why wouldn't this be considered a reduction? Not sure if this is a hard and fast rule or just a shortcut that works most of the time. The resonance forms stabilize the enolate, further increasing the acidity of the α hydrogen.