Chapter 21, Problem 41P

Compound W was isolated from a marine annelid commonly used in Japan as a fish bait, and it was shown to be the substance that gives this organism its observed toxicity to some insects that contact it.

MS (m/z): 151 (relative abundance 0.09), 149 ( ${\text{M}}^{\begin{array}{l}+\\ .\end{array}}$, rel. abund. 1.00), 148

IR (cm⁻¹): 2960, 2850, 2775

¹H NMR (δ): 2.3 (s, 6H), 2.6 (d, 4H), and 3.2 (pentet, 1H)

¹³C NMR (δ): 38 (CH₃), 43 (CH₂), and 75 (CH)

These reactions were used to obtain further information about the structure ofW:

Compound X had a new infrared band at 2570 cm⁻¹and these NMR data:

¹H NMR(δ): 1.6 (t, 2H), 2.3 (s, 6H), 2.6 (m, 4H), and 3.2 (pentet, 1H)

¹³C NMR(δ): 28 (CH₂), 38 (CH₃), and 70 (CH)

Compound Y had these data:

IR (cm⁻¹): 3050, 2960, 2850, 1700, 1610, 1500, 760, 690

¹H NMR (δ): 2.3 (s, 6H), 2.9 (d, 4H), 3.0 (pentet, 1H), 7.4 (m, 4H), 7.6 (m, 2H), and 8.0 (m, 4H)

¹³C NMR (δ): 34 (CH₂), 39 (CH₃), 61 (CH), 128 (CH), 129 (CH), 134 (CH), 135 (C), and 187 (C)

Compound Z had

MS (m/z): 87 ( ${\text{M}}^{\begin{array}{l}+\\ .\end{array}}$), 86, 72

IR (cm⁻¹): 2960, 2850, 1385, 1370, 1170

¹H NMR (δ): 1.0 (d, 6H), 2.3 (s, 6H), and 3.0 (heptet, 1H)

¹³C NMR (δ): 21 (CH₃), 39 (CH₃), and 55 (CH)

What are the structures of W and of each of its reaction products X, Y, and Z?