i) Under conditions B, the mono-methylated product 16 is formed. Draw a mechanism to explain this outcome. What does the position of methylation tell you? (2 marks)

ii) Under conditions C, the decomposition product 17 is formed. Draw a mechanism to explain this outcome. Why does the change in reaction conditions (relative to A) open this alternative pathway? (4 marks)

 

Ar A N C. 1.2x CHLI, -78 c Ph. .D i. DO 15 Os Ar B Os5-Ar .N. 1.2x CHLI, -78 c . 1x CHJ . HO (work-up) Ph. N H. Ph. 14 16 D 1.2XCHLI, 25 C i. D0 Ph. 17 O=-Z