Question

Treatment of ketoaldehyde 13 with aq. NaOH in dilute solution gave product 14.Its IR and NMR spectra showed OH and C=0 groups, but no aldehyde H. Draw the structure of

14 and use "curly arrows to show the mechanism of reaction.Briefly explain why 14 does not dehydrate to C9H120. O Suggest a synthetic route from the starting materials 15 and 16 to the epoxy ketone17. You can use any reagents/catalysts that you have met in your studies at University.

Question image 1Question image 2Question image 3Question image 4