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Answers
The keto form is more stable in single carbonyl carbon containing compounds as the carbon-oxygen pi bond is stronger and hence more stable than the carbon-carbon pi bond.
Although the keto form is most stable for aldehydes and ketones in most situations, there are several factors that will shift the equilibrium toward the enol form.
1. Aromaticity- Phenols can theoretically exist in their keto forms, but the enol form is greatly favored due to aromatic stabilization.
2. Hydrogen Bonding.- hydrogen bond acceptors stabilize the enol form. When a Lewis basic group is nearby, the enol form is stabilized by internal hydrogen bonding.
3. Solvent - Example - In a polar protic solvent like water, the lone pairs will be involved in hydrogen bonding with the solvent, making them less available to hydrogen bond with the enol form.
4. Conjugation - stability due to conjugattion , the resonance
5. Substitution.- In the absence of steric factors, increasing substitution at carbon will stabilize the enol form. Enols are alkenes too - so any factors that stabilize alkenes, will stabilize enols as well. All else being equal, double bonds increase in thermodynamic stability as substitution is increased.