Concept explainers
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.
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Organic Chemistry
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