Question

1. A Robinson annulation is a reaction that involves: (i) a Michael addition of an enolate onto an ,ß-unsaturated enone followed by (ii) an intramolecular aldol reaction. The molecule shown below (cyclohexenone X) can be made through two different Robinson annulation reactions. (A) Show the two different sets of starting materials (i.e. ketone 1 &a,p-unsaturated enone 1 and ketone 2 & a,B-unsaturated enone 2) for each Robinson annulation. Draw the reagents/reaction conditions. (B) Then pick one set and draw an arrow.pushing mechanism to show how the starting materials are converted to the final product (cyclohexenone X). cyclohexemonex 2. The following reaction was performed and the 'H NMR spectrum of the product was obtained mo CHCN (0,5 days (A) Identify the product Z, which is the structure of the spectrum obtained. (B) Assign the diagnostic protons in the structure of your product Z in the 'H NMR spectrum. (C) Draw a stepwise arrow pushing mechanism of how the product Z is formed from the given reaction conditions. 'H NMR spectrum of Compound Z

Answer 1

1(a) Keton x, Bunsaturated enone 1 or + Hg the city Ketone X, B-unsaturated eone 2

modi note Etow Na oEt CHg PI CH2 HOEE EtOH I NaOH (104) Ce HTOH HO -H2Of Naon