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- https://chem.libretexts.org/Courses/Oregon_Institute_of_Technology/OIT_(Lund)%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)/07%3A_Acid-base_Reactions/7.06%3A_Carbon_AcidsSo far, we have limited our discussion of acidity and basicity to heteroatom acids, where the acidic proton is bound to an oxygen, nitrogen, sulfur, or halogen. However, carbon acids - in which the pr...So far, we have limited our discussion of acidity and basicity to heteroatom acids, where the acidic proton is bound to an oxygen, nitrogen, sulfur, or halogen. However, carbon acids - in which the proton to be donated is bonded to a carbon atom - play an integral role in biochemistry.
- https://chem.libretexts.org/Courses/Smith_College/CHM_222_Chemistry_II%3A_Organic_Chemistry_(2025)/16%3A_Alkynes_-_An_Introduction_to_Organic_Synthesis/16.05%3A_Hydration_of_AlkynesAs with alkenes, hydration (addition of water) to alkynes requires a strong acid, usually sulfuric acid, and is facilitated by mercuric sulfate. However, unlike the additions to double bonds which giv...As with alkenes, hydration (addition of water) to alkynes requires a strong acid, usually sulfuric acid, and is facilitated by mercuric sulfate. However, unlike the additions to double bonds which give alcohol products, addition of water to alkynes gives ketone products ( except for acetylene which yields acetaldehyde ). The explanation for this deviation lies in enol-keto tautomerization.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(Morsch_et_al.)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.01%3A_Keto-Enol_TautomerismThis causes the pi electrons of the protonated carbonyl to move to the oxygen to form the hydroxyl group of the enol product and regenerating the acid catalyst. The positioning of the enol and the car...This causes the pi electrons of the protonated carbonyl to move to the oxygen to form the hydroxyl group of the enol product and regenerating the acid catalyst. The positioning of the enol and the carbonyl prevents the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen.
- https://chem.libretexts.org/Courses/SUNY_Oneonta/Organic_Chemistry_with_a_Biological_Emphasis_(SUNY_Oneonta)/07%3A_Acid-base_Reactions/7.07%3A_Carbon_AcidsSo far, we have limited our discussion of acidity and basicity to heteroatom acids, where the acidic proton is bound to an oxygen, nitrogen, sulfur, or halogen. However, carbon acids - in which the pr...So far, we have limited our discussion of acidity and basicity to heteroatom acids, where the acidic proton is bound to an oxygen, nitrogen, sulfur, or halogen. However, carbon acids - in which the proton to be donated is bonded to a carbon atom - play an integral role in biochemistry.
- https://chem.libretexts.org/Courses/University_of_Alberta_Augustana_Campus/AUCHE_252_-_Organic_Chemistry_II/05%3A_Aldehydes_and_Ketones/5.01%3A_Keto-Enol_TautomerismThe positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. This causes the pi electro...The positioning of the carbonyl groups allows for the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen. This causes the pi electrons of the protonated carbonyl to move to the oxygen to form the hydroxyl group of the enol product and regenerating the acid catalyst.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.01%3A_Keto-Enol_TautomerismThis causes the pi electrons of the protonated carbonyl to move to the oxygen to form the hydroxyl group of the enol product and regenerating the acid catalyst. The positioning of the enol and the car...This causes the pi electrons of the protonated carbonyl to move to the oxygen to form the hydroxyl group of the enol product and regenerating the acid catalyst. The positioning of the enol and the carbonyl prevents the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.01%3A_Keto-Enol_TautomerismThe page on keto-enol tautomerism describes the equilibrium between keto (carbonyl) and enol (alkene with an alcohol) forms of carbonyl compounds. This process involves the transfer of a proton and th...The page on keto-enol tautomerism describes the equilibrium between keto (carbonyl) and enol (alkene with an alcohol) forms of carbonyl compounds. This process involves the transfer of a proton and the movement of a double bond, affecting the compound's reactivity and stability. Factors like solvent and temperature can influence the tautomeric ratio. Understanding this equilibrium is crucial for predicting reaction outcomes in organic synthesis.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/09%3A_Alkynes_-_An_Introduction_to_Organic_Synthesis/9.04%3A_Hydration_of_AlkynesAs with alkenes, hydration (addition of water) to alkynes requires a strong acid, usually sulfuric acid, and is facilitated by mercuric sulfate. However, unlike the additions to double bonds which giv...As with alkenes, hydration (addition of water) to alkynes requires a strong acid, usually sulfuric acid, and is facilitated by mercuric sulfate. However, unlike the additions to double bonds which give alcohol products, addition of water to alkynes gives ketone products ( except for acetylene which yields acetaldehyde ). The explanation for this deviation lies in enol-keto tautomerization.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_I_(Morsch_et_al.)/09%3A_Alkynes_-_An_Introduction_to_Organic_Synthesis/9.04%3A_Hydration_of_AlkynesAs with alkenes, hydration (addition of water) to alkynes requires a strong acid, usually sulfuric acid, and is facilitated by mercuric sulfate. However, unlike the additions to double bonds which giv...As with alkenes, hydration (addition of water) to alkynes requires a strong acid, usually sulfuric acid, and is facilitated by mercuric sulfate. However, unlike the additions to double bonds which give alcohol products, addition of water to alkynes gives ketone products ( except for acetylene which yields acetaldehyde ). The explanation for this deviation lies in enol-keto tautomerization.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.02%3A_Keto-Enol_TautomerismThis also causes the pi bond electrons from the enol double bond to attack the electrophilic H + provided by acid catalyst forming a C-H bond in the α-position This produced oxonium intermediate is su...This also causes the pi bond electrons from the enol double bond to attack the electrophilic H + provided by acid catalyst forming a C-H bond in the α-position This produced oxonium intermediate is subsequently deprotonated to form the neutral ketone and regenerate the acid catalyst. The positioning of the enol and the carbonyl prevents the formation of a stabilizing intramolecular hydrogen bond between the hydroxyl group of the enol and the carbonyl oxygen.
- https://chem.libretexts.org/Courses/Oregon_Institute_of_Technology/OIT%3A_CHE_332_--_Organic_Chemistry_II_(Lund)/7%3A_Acid-base_Reactions/7.6%3A_Carbon_AcidsSo far, we have limited our discussion of acidity and basicity to heteroatom acids, where the acidic proton is bound to an oxygen, nitrogen, sulfur, or halogen. However, carbon acids - in which the pr...So far, we have limited our discussion of acidity and basicity to heteroatom acids, where the acidic proton is bound to an oxygen, nitrogen, sulfur, or halogen. However, carbon acids - in which the proton to be donated is bonded to a carbon atom - play an integral role in biochemistry.
