Organic Chemistry As a Second Language: Second Semester Topics
4th Edition
ISBN: 9781119110651
Author: David R. Klein
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 3.1, Problem 3.11P
If you look at your answers to the previous problems, you should find that one of the structures was expected to produce an NMR spectrum with only one signal. In that structure (problem 3.4), all six methyl groups were chemically equivalent. Using that example as guidance, propose two possible structures for a compound with molecular formula C9H18 that exhibits an NMR spectrum with only one signal.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
use the attached NMR spectrum to generate the structural formula of the compound .Unknown NMR # 8 was found to be a methyl ketone .Please write down your analysis of each peak and what it corresponds to. After analyzing each peak at whatever ppm, splitting pattern and integration, you should successfully draw the structure of the type alcohol compound
From the 13C spectrum of a compound, one can assign signals to specific carbon atoms of the compound and determine the number of protons on each of
those carbon atoms. Such information in conjunction with the DEPT C-13 chart will allow the appearance of the corresponding DEPT spectrum of the
compound to be predicted. There are five signals (I – V) in the 13C spectrum of compound A as shown below. At the exactly same location of each of these five
signals, "a peak", "no peak", or "an inverted peak" may appear in the corresponding DEPT-135 spectrum. Predict the DEPT-135 spectrum of compound A by
selecting the expected signal appearance at each of these five locations in the DEPT-135 spectrum.
-
II
II
IV
V
in
HO
A
100
PPM
180
160
140
120
80
60
40
20
v At the location of signal I
A. no peak
v At the location of signal IIl
В. а рeak
v At the location of signal IIl
C. an inverted peak
v At the location of signal IV
v A the location of signal V
Two bottles labelled cis-cyclohexandiol were found in a
laboratory. Because of their differing melting points, the
bottles clearly contained two different cis-cyclohexandiol
isomers. To determine which isomer was in which bottle,
the chemist decided to run ¹3C NMR spectra on a
sample of each. The three possible products were as in
the figure. (Figure 1)
The two ¹³C NMR proton-decoupled spectra contained
the following data:
●
●
Figure
HO
spectrum of sample in bottle A: 20.20,
62.55
spectrum of sample in bottle B: 16.09,
29.52, 36.15, 63.08
OH
OH
OH
1 of 1
OH
OH
Part A
Identify which isomer was present in the bottle A.
OH
HO
OH
OH
OH
OH
Chapter 3 Solutions
Organic Chemistry As a Second Language: Second Semester Topics
Ch. 3.1 - Prob. 3.2PCh. 3.1 - Prob. 3.3PCh. 3.1 - Prob. 3.4PCh. 3.1 - Prob. 3.5PCh. 3.1 - Prob. 3.6PCh. 3.1 - Prob. 3.7PCh. 3.1 - Prob. 3.8PCh. 3.1 - Prob. 3.9PCh. 3.1 - Prob. 3.10PCh. 3.1 - If you look at your answers to the previous...
Ch. 3.2 - Predict the chemical shifts for the signals in the...Ch. 3.2 - Predict the chemical shifts for the signals in the...Ch. 3.2 - Predict the chemical shifts for the signals in the...Ch. 3.2 - Predict the chemical shifts for the signals in the...Ch. 3.2 - Predict the chemical shifts for the signals in the...Ch. 3.2 - Predict the chemical shifts for the signals in the...Ch. 3.2 - Prob. 3.19PCh. 3.3 - Prob. 3.21PCh. 3.3 - Prob. 3.22PCh. 3.3 - Prob. 3.23PCh. 3.4 - Predict the multiplicity of each signal in the...Ch. 3.4 - Predict the multiplicity of each signal in the...Ch. 3.4 - Predict the multiplicity of each signal in the...Ch. 3.4 - Predict the multiplicity of each signal in the...Ch. 3.4 - Predict the multiplicity of each signal in the...Ch. 3.4 - Predict the multiplicity of each signal in the...Ch. 3.5 - Below are NMR spectra of several compounds....Ch. 3.5 - Below are NMR spectra of several compounds....Ch. 3.5 - Below are NMR spectra of several compounds....Ch. 3.8 - Calculate the degree of unsaturation for each of...Ch. 3.8 - Calculate the degree of unsaturation for each of...Ch. 3.8 - Calculate the degree of unsaturation for each of...Ch. 3.8 - Calculate the degree of unsaturation for each of...Ch. 3.8 - Calculate the degree of unsaturation for each of...Ch. 3.8 - Calculate the degree of unsaturation for each of...Ch. 3.9 - Prob. 3.43PCh. 3.9 - Propose a structure for a compound with molecular...Ch. 3.9 - Propose a structure for a compound with molecular...Ch. 3.9 - Propose a structure for a compound with molecular...Ch. 3.9 - Propose a structure for a compound with molecular...Ch. 3.9 - Prob. 3.48PCh. 3.10 - For each compound below, predict the number of...Ch. 3.10 - For each compound below, predict the number of...Ch. 3.10 - For each compound below, predict the number of...Ch. 3.10 - For each compound below, predict the number of...Ch. 3.10 - For each compound below, predict the number of...Ch. 3.10 - For each compound below, predict the number of...
Additional Science Textbook Solutions
Find more solutions based on key concepts
Compute the empirical and molecular formulas for each of the following elemental analyses In each case, propose...
Organic Chemistry (9th Edition)
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
4. 38 Strontium has four naturally occurring isotopes, with mass numbers 84, 86, 87, arid 88.
a. Write the atom...
General, Organic, and Biological Chemistry: Structures of Life (5th Edition)
35. Consider the reaction.
The graph shows the concentration of Br2 as a function of time.
a. Use the g...
Chemistry: Structure and Properties
11.47. Vicinal halo alcohols (halohydrins) can be synthesized by treating epoxides with HX.
(a) Show how you ...
Organic Chemistry
1.1 Write a one-sentence definition for each of the following:
a. chemistry
b. chemical
Chemistry: An Introduction to General, Organic, and Biological Chemistry (12th Edition) - Standalone book
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
- The 1H-NMR spectrum of 1-bromopropane shows three signals and the 1H-NMR spectrum of 2-bromopropane shows two signals. Draw these two molecules and determine the relative integrals of each signal.arrow_forwardComplete the spectroscopy data tables for a compound with molecular formula C6H14. Determine the structure of the compound. Any labile protons, if they exist, will not be present in this particular 1H NMR spectrum.arrow_forwardDraw the structural formulas of the following compounds and indicate the number of NMR signals that would be expected for each compound. (a) methyl iodide (b) 2,4-dimethylpentane (c) cyclopentane (d) propylene (propene)arrow_forward
- 6) Complete the spectroscopy data tables for a compound with molecular formula C6H12O. Determine the structure of the compound. Any labile protons, if they exist, will not be present in this particular 1H NMR spectrum.arrow_forwardCompound 1 has molecular formula C6H12. It shows three signals in the 1H-NMR spectrum, one at 0.96 ppm, one at 2.03 ppm, and one at 5.33 ppm. The relative integrals of these three signals are 3, 2, and 1, respectively. Compound 2 has molecular formula C7H15Br. It shows two signals in the 1H-NMR spectrum, one at 1.08 ppm and one at 1.59 ppm. The relative integrals of these two signals are 3 and 2, respectively. Propose structures for compounds 1 and 2, explaining how you reach your conclusion.arrow_forward1Compound 1 has molecular formula C7H16. It shows three signals in the 1H-NMR spectrum, one at 0.85 ppm, one at 1.02 ppm, and one at 1.62 ppm. The relative integrals of these three signals are 6, 1, and 1, respectively. Compound 2 has molecular formula C7H14. It shows three signals in the 1H-NMR spectrum, one at 0.98 ppm, one at 1.36 ppm, and one at 1.55 ppm. The relative integrals of these three signals are 3, 2, and 2, respectively. Propose structures for compounds 1 and 2, explaining how you reach your conclusion.arrow_forward
- Please solve this organic chemistry question A carboxylic acid with the molecular formula C5H10O2 is treated with thionyl chloride to give compound A. Compound A has only one signal in its 1H NMR spectrum. Please figure out this carboxylic acid. You can write out name directly or molecular formula with functional groups (e.g. isopropanol (CH3)3COH). Hint: Only one H NMR signal means all hydrogens are in the same chemical status.arrow_forward(3) These natural compounds will have different numbers of 1H-NMR signals in different NMR solvents like CDC13 and methanol-d4. How many signals do you anticipate for each compound respectively in CDC13 and methanol-d4? LOCH 3 OHC. vanillin OH LOH acetoaminophen HO thymolarrow_forwardThe 1H and 13C NMR for a compound with the formula C5H12O are shown. Determine the structure of this compound. Assign the peaks: assign “a” to the most shielded hydrogen(s) in your structure, “b” to next-most shielded, etc; use capital letters for carbons).arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Physical ChemistryChemistryISBN:9781133958437Author:Ball, David W. (david Warren), BAER, TomasPublisher:Wadsworth Cengage Learning,
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Physical Chemistry
Chemistry
ISBN:9781133958437
Author:Ball, David W. (david Warren), BAER, Tomas
Publisher:Wadsworth Cengage Learning,
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Mass Spectrometry; Author: Professor Dave Explains;https://www.youtube.com/watch?v=hSirWciIvSg;License: Standard YouTube License, CC-BY