Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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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 ( m/z ) : 151 (relative abundance 0.09), 149 ( M . + , rel. abund. 1.00), 148

IR ( c m 1 ) : 2960, 2850, 2775

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

1 3 C NMR ( δ ) : 38 ( C H 3 ) ,   43   ( C H 2 ) ,   a n d   75   ( C H )

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

W N a B H 4 X C 6 H 5 C O C l Y R a n e y N i Z

Compound X had a new infrared band at 2570 c m 1 and these NMR data:

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

13C NMR ( δ ) : 28 ( C H 2 ) ,   38 ( C H 3 ) ,   a n d   70 ( C H )

Compound Y had these data:

IR ( c m 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 ( C H 2 ) ,   39 ( C H 3 ) ,   61 ( C H ) ,   128 ( C H ) ,   129 ( C H ) ,   134 ( C H ) , 135 (C), and 187 (C)

Compound Z had

MS ( m/z ) : 87 ( M . + ), 86, 72

IR ( c m 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 ( C H 3 ) ,   39 ( C H 3 ) ,   a n d   55 ( C H )

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

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