Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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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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An organic compound has a percent composition, 89.84 %C, 10.17 %H. This compound has an
approximate boiling point of 152 °C at 757 mmHg. The IR spectrum of the neat thin film is shown below.
Propose a structure of this compound and show your rational for full credit.
LD
3084
G2
2071
1166
42
1201
77
1028
44
3064
53
1942
84
14E0
53
1213
84
922
81
3028
37
186
86
1452
31
1150
86
905
79
3002
68
1800
84
1384
62
1144
86
BOTT
81
62
2961
7
1604
62
1364 57
699
4
2927
35
1583
84
1923
1082
555
Б4
2090
46
1494
20
1100
67
479
B4
D
4000
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TRANSHITTANCEIXI
A hydrocarbon, compound B, has molecular formula C6H6, and gave an NMR spectrum with two signals: delta 6.55 pm and delta 3.84 pm with peak ratio of 2:1. When warmed in pyridine for three hr, compound B quantitatively converts to benzene. Mild hydrogenation of B yielded another compound C with mass spectrum of m/z 82. Infrared spectrum showed no double bonds; NMR spectrum showed one broad peak at delta 2.34 ppm. With this information, address the following questions.
a) How many rings are in compound C?
b) How many rings are probably in B? How many double bonds are in B?
c) Can you suggest a structure for compounds B and C?
d) In the NMR spectrum of B, the up-field signal was a quintet, and the down field signal was a triplet. How must you account for these splitting patterns?
Infrared red spectroscopy is based on the absorption of infrared addition. Only molecules that under a change in dipole moment are IR active. Explain what is meant by dipole moment of a molecule
Certain molecules like N2 (NN) do not absorb IR, explain why?
What causes the OH peak to be broad and how can this be prevented?
The IR spectra of a nitrogenous fertilizer and an ingredient in soap are shown below. Identify the functional groups in both compounds. Justify your answers.
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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