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- 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/Martin_Luther_College/Organic_Chemistry_-_MLC/03%3A_Alcohols_Ethers_Thiols_Sulfides_and_Amines/3.01%3A_Alcohols_and_Phenols/3.1.01%3A_IntroductionThe structure of the simplest alcohol, methanol (methyl alcohol), can be derived from that of methane by putting an OH in place of one of the H’s: Ethanol makes up 3 to 6 percent of beer, 12 to 15 per...The structure of the simplest alcohol, methanol (methyl alcohol), can be derived from that of methane by putting an OH in place of one of the H’s: Ethanol makes up 3 to 6 percent of beer, 12 to 15 percent of most wines, and 49 to 59 percent of distilled liquor. (The “proof” of an alcoholic beverage is just twice the percentage of ethanol.) Alcohol’s intoxicating effects are well known, and it is a mild depressant.
- 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_(OpenStax)/17%3A_Alcohols_and_Phenols/17.00%3A_Why_This_ChapterAlcohols and phenols can be thought of as organic derivatives of water in which one of water’s hydrogens is replaced by an organic group: H–O–H versus R–O–H and Ar–O–H. In practice, the name alcohol i...Alcohols and phenols can be thought of as organic derivatives of water in which one of water’s hydrogens is replaced by an organic group: H–O–H versus R–O–H and Ar–O–H. In practice, the name alcohol is restricted to compounds that have their –OH group bonded to a saturated, sp³-hybridized carbon atom, while compounds with their –OH group bonded to a vinylic, sp²-hybridized carbon are called enols.
- 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)/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_(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/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/17%3A_Alcohols_and_Phenols/17.01%3A_IntroductionThe structure of the simplest alcohol, methanol (methyl alcohol), can be derived from that of methane by putting an OH in place of one of the H’s: Ethanol makes up 3 to 6 percent of beer, 12 to 15 per...The structure of the simplest alcohol, methanol (methyl alcohol), can be derived from that of methane by putting an OH in place of one of the H’s: Ethanol makes up 3 to 6 percent of beer, 12 to 15 percent of most wines, and 49 to 59 percent of distilled liquor. (The “proof” of an alcoholic beverage is just twice the percentage of ethanol.) Alcohol’s intoxicating effects are well known, and it is a mild depressant.
- 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.
