Problems and exercisesEnolization and enolate ions

Rank the indicated hydrogens in order of increasing acidity: (a) CH₃CO₂Et; (b) CH₃COCH₂COCH₃ (the CH₂); (c) CH₃COCH₃; (d) CH₃NO₂. Justify the order.

Explain why LDA in THF at −78 °C, rather than sodium ethoxide in ethanol, is used to alkylate cyclohexanone with methyl iodide.

The potassium enolate of cyclohexanone in HMPA reacts with dimethyl sulfate to give mainly 1-methoxycyclohexene; the lithium enolate in THF reacts with methyl iodide to give 2-methylcyclohexanone. Explain the difference.