Which enol form of ethyl 3-oxobutanoate is predominant at equilibrium? K Your answer: но OEt d) Correct answer: OH OEt b) Feedback: For enolate ions of 1,3-dicarbonyl compounds, see pp. 392-393. Conjugation of the C=C double bond with the remaining carbonyl provides a more stable enol, which rules out (a). Enols (b)-(d) may all be obtained by protonation of the same enolate or the readily interconverting stereoisomeric enolates. Of these, (b) and (d) allow stabilizing intramolecular hydrogen bonding; (b) is the more stable of the two owing to the conjugative stability of the remaining ester group.

In the following acid - base reactions, a) Draw Lewis structures of the reactants and the products. b) Determine which species are acting as electrophiles (acids) and which are acting as nucleophiles (bases). c) Use the curved - arrow formalism to show the movement of electron pairs in these reactions and the imaginary movement in the resonance hybrids of the products. d) Indicate which reactions are best termed Brønsted-Lowry acid - base reactions i. CH3CHO + HCI-- > CH3CH2O + + Cl- ii. CH3CHO + OH- - - > CH3CO-(OH) H

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Why is HCl so acidic? For example, why is H-Cl more acidic than H-S-CH3? Isn't the conjugate base's negative charge more stabilized with a sulfur and extra methyl group (by the induction effect)? While Cl is more electronegative than Sulfur, I would assume Cl being alone as its own ion would make it less stable.