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

Spectral data for B:
MS (m/z): 314, 312, 310 (relative abundance 1:2:1)
1H NMR (δ): only 6.80 (s) after treatment with D2O
Data for C:
MS (m/z): 371, 369, 367 (relative abundance 1:2:1)
1H NMR (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 for D:
MS (m/z): 369 (M+.- CH3) [when studied as its tris(trimethylsilyl) derivative]
1H NMR (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.

Transcribed Image Text:

COOH Br HCHO Raney Ni/H2 water D он