Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Question
Chapter 23, Problem 24P
Interpretation Introduction
Interpretation:
The structures for the compounds in the given reaction sequence are to be determined.
Concept introduction:
Ostracian lentiginosus, commonly known as boxfish or pahu, is found in Hawaiin beaches. It secretes a toxic chemical that kills other fish that comes in its vicinity.
The main chemical responsible for toxicity was named by P.J. Scheurer as pahutoxin. This chemical contained a combination of lipid moieties.
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TRANSHITTANCEIXI
20) An unknown compound has the chemical formula CH₂O. It's IR spectrum and ¹H NMR
spectrum are shown below. Propose a structure for the unknown molecule. Calculate the
Degrees of Unsaturation (DU), assign any important peaks in the IR spectrum to vibrational
modes and briefly explain why the structure fits the 'H NMR spectrum that is provided
Degrees of unsaturation (show work below):
442
Du= (2(3)+2)-6
2
-8-16 - 2²/2/2 = 1
3437
1739
Amply
0
Vibrational Assignments of IR Peaks
Wavenumber (cm-¹) Vibrational Assignment
0-4 stretch
6=0 strekh
Peak 1:
9.79 ppm
14
Singlet
3
8
Brief rationalization for proposed structure: (explain why DU, IR, and
NMR are consistent with proposed structure)
ppm
Peak 2
2.45 ppm
2H
Quartet
Peak 3
1.11 ppm
3H
Triplet
D
Proposed structure of unknown:
Chapter 23 Solutions
Organic Chemistry
Ch. 23 - Prob. 1PPCh. 23 - Prob. 2PPCh. 23 - Prob. 3PPCh. 23 - Prob. 4PPCh. 23 - Prob. 5PPCh. 23 - Prob. 6PPCh. 23 - Prob. 7PPCh. 23 - Prob. 8PPCh. 23 - Prob. 9PPCh. 23 - Prob. 10PP
Ch. 23 - Prob. 11PPCh. 23 - Prob. 12PCh. 23 - 23.15 How would you transform tetradecanal into...Ch. 23 - Prob. 14PCh. 23 - Prob. 15PCh. 23 - When limonene (Section 23.3) is heated strongly,...Ch. 23 - Gadoleic acid (C20H38O2), a fatty acid that can be...Ch. 23 - 23.20 -Phellandrene and -phellandrene are isomeric...Ch. 23 - Prob. 19PCh. 23 - Prob. 20PCh. 23 - Prob. 21PCh. 23 - The initial steps of a laboratory synthesis of...Ch. 23 - Prob. 23PCh. 23 - Prob. 24PCh. 23 - Prob. 25PCh. 23 - 2. The biosynthesis of fatty acids is accomplished...Ch. 23 - Prob. 3LGPCh. 23 - Prob. 4LGPCh. 23 - 23.1 Write an appropriate formula in each box.
Ch. 23 - Give a reagent that would distinguish between each...Ch. 23 - 23.3 What product would be obtained by catalytic...Ch. 23 - Prob. 4QCh. 23 - 23.5 The following compound is a:
(a)...Ch. 23 - Mark off the isoprene units in the previous...Ch. 23 - Prob. 7Q
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