Chapter SRP, Problem 33P

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

Spectral data for B:

$\begin{array}{l}MS\left(m/z\right)\text{: 314, 312, 310 }\left(\text{relative abundance 1:2:1}\right)\\ {}^{\text{1}}\text{H NMR }\left(\text{δ}\right)\text{: only 6}\text{.80 }\left(\text{s}\right){\text{ after treatment with D}}_{\text{2}}\text{O}\\ \text{ Data for C:}\\ MS\left(m/z\right)\text{: 371, 369, 367 }\left(\text{relative abundance 1:2:1}\right)\\ {}^{\text{1}}\text{H NMR }\left(\text{δ}\right)\text{: 2}\text{.48 }\left(\text{s}\right)\text{ and 4}\text{.99 }\left(\text{s}\right)\text{ in area ratio 3:1; broad singlets at 5}{\text{.5 and 11 disappeared after treatment with D}}_{\text{2}}\text{O}\text{. }\\ \text{Data for D:}\end{array}$

$\begin{array}{l}MS\text{ (}m/z)\text{: 369 (M}{\cdot }^{+}-{\text{CH}}_{\text{3}}\text{) [when studied as its tris(trimethylsilyl) derivative]}\\ {}^{\text{1}}\text{H NMR (d): 2}\text{.16 (s) and 7}\text{.18 (s) in area ratio 3:2; broad singlets at }\\ \text{5}{\text{.4 and 11 disappeared after treatment with D}}_{\text{2}}\text{O}\text{.}\end{array}$