Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 23, Problem 26P
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.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
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
3000
2000
1500
1000
500
TRANSHITTANCEIXI
The IR and NMR spectra of the material whose structure formula is C16H22O4 are given below.To this datawhat could be the ingredient?
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. 12PPCh. 23 - Prob. 13PPCh. 23 - Prob. 14PCh. 23 - 23.15 How would you transform tetradecanal into...Ch. 23 - Prob. 16PCh. 23 - Prob. 17PCh. 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. 21PCh. 23 - Prob. 22PCh. 23 - Prob. 23PCh. 23 - The initial steps of a laboratory synthesis of...Ch. 23 - Prob. 25PCh. 23 - Prob. 26PCh. 23 - Prob. 27PCh. 23 - 2. The biosynthesis of fatty acids is accomplished...Ch. 23 - Prob. 3LGPCh. 23 - Prob. 4LGP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- A certain compound was known to have a formula which could be represented as [PdCxHyN₂ ](ClO4)2. Analysis showed that the compound contained 30.15% carbon, 5.06% hydrogen. When converted to the corresponding thiocyanate, [PdC₂H₂N₂ ](SCN)₂, the analysis was 40.46% carbon and 5.94% hydrogen. Calculate the value of x, y, and z. Ox=14, y = 28, z= 4 x = 28, y = 4, z= 14 Ox= 14, y = 4, z= 28 O x = 4, y = 14, z = 28arrow_forwardThe IR spectrum, 1H NMR spectrum, and 13C NMR spectrum for the unknown compound with the formula C5H12O are given below. Make a structure for the unknown and assign the peaks in the spectra by the provided tables.arrow_forwardA certain compound was known to have a formula which could be represented as [PdCxHyN₂ ](ClO4)2. Analysis showed that the compound contained 30.15% carbon, 5.06% hydrogen. When converted to the corresponding thiocyanate, [PdC₂H₂N₂ ](SCN)₂, the analysis was 40.46% carbon and 5.94% hydrogen. Calculate the value of x, y, and z.arrow_forward
- Ketones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+=74 in the mass spectrum?arrow_forwardIR spectroscopy played a key role in elucidating the structure of penicillin G. Explain why the carbonyl on β-Lactams absorbs at ~1760 cm −1, which is much higher than observed in most of other amides.arrow_forwardCaffeine is a common organic molecule found in many beverages such as coffee, tea,and cola. It is a stimulant to the central nervous system. That is why many students drink coffee or soda to help them feel alert.Like many conjugated organic molecules, caffeine absorbs radiation with a wavelength around 260 nm.In this analysis, the class of Ms Judy determined the caffeinecontentin Red Bull energy drinkusing UV-vis spectroscopy a. .Construct a calibration curve. b.What is the concentration of caffeine in the unknown sample? c. Complete the tablearrow_forward
- The two compounds 1,2-dibromobenzene and 1 3-dibromobenzene both have the molecular formula C6H4Brz. a)Draw the chemical structures of the two molecules. b)Can these two molecules be distinguished by 1H NMR spectroscopy? Give reasons for your answer and describe the number of proton environments and their splitting for both molecules. Can these two molecules be distinguished by 13C NMR spectroscopy? Give reasons for your answer. Can these two molecules be distinguished by IR spectroscopy? Give reasons for your answer and describe the main IR signals (with frequencies) you expect to see for both molecules. Can these two molecules be distinguished by mass spectrometry? Give reasons for your answer.arrow_forwarddescribe/ analyze the IR spectra pattern of salicylic acidarrow_forwardInfrared 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.arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning