a) Under conditions A, the doubly-deuterated product 15 is formed. Draw a mechanism to explain this outcome.

b) 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?

c) 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?

Transcribed Image Text:

Ozğ. Ar A N° 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) .N. N° Ph. Ph. 14 16 D 1.2XCHLI, 25 °C i. D0 Ph. 17 え エ Ozğ. Ar A N° 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) .N. N° Ph. Ph. 14 16 D 1.2XCHLI, 25 °C i. D0 Ph. 17 え エ