Chapter SRP, Problem 37P

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 $\left(\text{m/z}\right)$: 151 (relative abundance 0.09), 149 ( $M_{.}^{+}$, rel. abund. 1.00), 148

IR $\left(c{m}^{-1}\right)$: 2960, 2850, 2775

${}^{1}H$ NMR $\left(\text{δ}\right)$: 2.3 $\left(s,6H\right),2.6\left(d,4H\right)$, and 3.2 (pentet, 1H)

${}^{13}C$ NMR $\left(\text{δ}\right)$: 38 $\left(CH3\right),43\left(CH2\right),and75\left(CH\right)$

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

$W\underset{}{\overset{NaB{H}_4}{\to }}X\underset{}{\overset{C_6{H}_{5}COCl}{\to }}Y\underset{}{\overset{RaneyNi}{\to }}Z$

Compound X had a new infrared band at 2570 $c{m}^{-1}$ and these NMR data:

${}^{1}H$ NMR $\left(\text{δ}\right)$: 1.6 (t, 2H), 2.3 (s, 6H), 2.6 (m, 4H), and 3.2 (pentet, 1H)

13C NMR $\left(\text{δ}\right)$: $28\left(C{H}_2\right),38\left(C{H}_3\right),and70\left(CH\right)$

Compound Y had these data:

IR $\left(c{m}^{-1}\right)$: 3050, 2960, 2850, 1700, 1610, 1500, 760, 690

1H NMR $\left(\text{δ}\right)$: 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 $\left(\text{δ}\right)$: 34 $\left(C{H}_2\right),39\left(C{H}_3\right),61\left(CH\right),128\left(CH\right),129\left(CH\right),134\left(CH\right)$, 135 (C), and 187 (C)

Compound Z had

MS $\left(\text{m/z}\right)$: 87 ( $M_{.}^{+}$), 86, 72

IR $\left(c{m}^{-1}\right)$: 2960, 2850, 1385, 1370, 1170

1H NMR $\left(\text{δ}\right)$: 1.0 (d, 6H), 2.3 (s, 6H), and 3.0 (heptet, 1H)

13C NMR $\left(\text{δ}\right)$: 21 $\left(C{H}_3\right),39\left(C{H}_3\right),and55\left(CH\right)$

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