Chapter 19, Problem 60P

Write the structures of the three products involved in this reaction sequence:

Spectral data forB:

MS(m/z): 314, 312, 310 (relative abundance 1:2:1)

¹HNMR(δ): only 6.80 (s) after treatment with D₂O

Data forC:

MS(m/z): 371, 369, 367 (relative abundance 1:2:1)

¹HNMR(δ): 2.48 (s) and 4.99 (s) in area ratio 3:1; broad singlets at 5.5 and 11 disappeared after treatment with D₂O.

Data forD:

MS(m/z):369(M+⋅−CH3) [when studied as its tris(trimethylsilyl) derivative]

¹HNMR(δ): 2.16 (s) and 7.18 (s) in area ratio 3:2; broad singlets at 5.4 and 11 disappeared after treatment with D₂O.