Carroll, pp 449 - 452: # 1, 2, 4, 5, 6, 7, 9, 11, 12, 13, 15, 17, 18, 22
1. Write a complete acid-catalyzed mechanism for the formation of cyclopropanone dimethyl ketal. Show all steps and all resonance forms for any intermediates involved.
Explain why cyclopropanone is much more reactive than cyclopentanone in this reaction, in particular identifying the mechanistic steps where there would be expected to be a significant difference.
2. If the base-catalyzed hydrolysis of methyl benzoate in O-18 labeled H2O is stopped before complete hydrolysis occurs, the recovered methyl benzoate includes some O-18. Explain with a complete mechanism.
Base-catalyzed hydrolysis of para-substituted methyl benzoates shows a Hammett correlation with a positive r value. Explain what conclusion might be drawn from this.