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Lol no I got the grasp of generating the 3d orbital diagrams in maple when at uni, but I'm not entirely sure how worth while that is for molecular interactions, but in the two dimensional the shaded/non shaded lobes seems like it could be handy
@@rojaslab haha well they are welcome to do so but be perpetually reassured by more and more empirical data if only i knew what I was attempting enrolling for a major in "chemical physics" 😂
@@rojaslab but I genuinely believe that should be the only way, sometimes theory results in experimentally determined conclusions and in other times we need to sit there and make theories based on experimentally determined values that are annoying us
how would you tautomerize the last Claisen rearrangement to form an alcohol for the last Practice problem? so, where would that double bond attached to the oxygen go?
Amazing question! I have a video coming out tomorrow that walks through the mechanism of keto-enol tautomerization. Until then, because of the acidity of α-hydrogens, many carbonyl containing compounds undergo a proton-transfer equilibrium called tautomerism. Tautomers are readily interconverted constitutional isomers, usually distinguished by a different location for an atom or a group. Because tautomers involve the rearrangement of atoms, they are distinctly different than resonance forms, which only differ in the position of bonds and lone pair electrons. This discussion focuses on carbonyl groups with α-hydrogens, which undergo keto-enol tautomerism. Keto implies that the tautomer contains a carbonyl bond while enol implies the presence of a double bond and a hydroxyl group. The keto-enol tautomerization equilibrium is dependent on stabilization factors of both the keto tautomer and the enol tautomer. For simple carbonyl compounds under normal conditions, the equilibrium usually strongly favors the keto tautomer (acetone, for example, is >99.999% keto tautomer). The keto tautomer is preferred because it is usually more stable than the enol tautomer by about 45-60 kJ/mol, which is mainly due to the C=O double bond (-749 kJ/mol) being stronger than the C=C double bond (-611 kJ/mol).
Here's a free resource showing the rearrangement also: chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.01%3A_Keto-Enol_Tautomerism
If you enjoyed this video, don't forget to give it a thumbs up, subscribe for more educational content, and hit the notification bell to stay updated! Have questions or specific topics you'd like me to cover? Drop them below, and let's keep the chemistry conversation going! #ScienceCommunity #LearningTogether #OrganicChemistry
Yeah I'll definitely need to adopt the orbital lobes into my diagrams
You’ve got this! 💪🏾
Lol no I got the grasp of generating the 3d orbital diagrams in maple when at uni, but I'm not entirely sure how worth while that is for molecular interactions, but in the two dimensional the shaded/non shaded lobes seems like it could be handy
@@Adam-l3f4f haha. Be careful. There are some chemists who would argue that the orbital interactions are the ONLY worthwhile thing to consider!
@@rojaslab haha well they are welcome to do so but be perpetually reassured by more and more empirical data if only i knew what I was attempting enrolling for a major in "chemical physics" 😂
@@rojaslab but I genuinely believe that should be the only way, sometimes theory results in experimentally determined conclusions and in other times we need to sit there and make theories based on experimentally determined values that are annoying us
how would you tautomerize the last Claisen rearrangement to form an alcohol for the last Practice problem? so, where would that double bond attached to the oxygen go?
Amazing question! I have a video coming out tomorrow that walks through the mechanism of keto-enol tautomerization. Until then, because of the acidity of α-hydrogens, many carbonyl containing compounds undergo a proton-transfer equilibrium called tautomerism. Tautomers are readily interconverted constitutional isomers, usually distinguished by a different location for an atom or a group. Because tautomers involve the rearrangement of atoms, they are distinctly different than resonance forms, which only differ in the position of bonds and lone pair electrons. This discussion focuses on carbonyl groups with α-hydrogens, which undergo keto-enol tautomerism. Keto implies that the tautomer contains a carbonyl bond while enol implies the presence of a double bond and a hydroxyl group.
The keto-enol tautomerization equilibrium is dependent on stabilization factors of both the keto tautomer and the enol tautomer. For simple carbonyl compounds under normal conditions, the equilibrium usually strongly favors the keto tautomer (acetone, for example, is >99.999% keto tautomer). The keto tautomer is preferred because it is usually more stable than the enol tautomer by about 45-60 kJ/mol, which is mainly due to the C=O double bond (-749 kJ/mol) being stronger than the C=C double bond (-611 kJ/mol).
Here's a free resource showing the rearrangement also: chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.01%3A_Keto-Enol_Tautomerism