Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 13, Problem 13.43SP
Interpretation Introduction
Interpretation:
The structure of the given NMR spectrum is to be shown and the appropriate peaks for the protons in the structure is to be assigned.
Concept introduction:
NMR spectroscopy is a technique used to determine a unique structure of the compounds. It identifies the carbon-hydrogen bonding of an organic compound. A hydrogen atom is called as a proton in the NMR spectroscopy.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
2
The IR and 1H-NMR spectra of a compound with molecular formula C4H7ClO2 are shown below. Your objective as a group is to propose a structure for this compound, explaining how you reach your decision. Using all the information you have been given, in a post with others in your group share your initial ideas about the possible structure of the compound. Then use comments to interact with the other students in the group and propose a final answer to the problem. In the comment phase, you should comment on the postings of at least two other students.
Analyze the ¹H NMR spectrum of methyl crotonate. Use the integrations, splitting patterns, and chemical shifts to assign the
protons for the structure.
HC
H3C
A
-7.271
7.013
6.974
6.939
s
J
1.01
7.0
5.873
5.869
-5.834
-5.830
[
HB
6.0
O
5.0
3.905
4.0
VCL C
3.07€
-3.538
CH3
D
T
3.0
f1 (ppm)
006
.894
-1.891
100
3.291
2.0
.877
1.874
.872
1.0
000*0-
B
0.0
© University of Michigan
Answer Bank
U
D
A
Dr. N. M. Arr was called in to help analyze the 1H NMR spectrum of a mixture of compounds known to contain only C, H, and Br. The mixture showed two singlets—one at 1.8 ppm and the other at 2.7 ppm—with relative integrals of 1 : 6, respectively. Dr. Arr determined that the spectrum was that of a mixture of bromomethane and 2-bromo-2-methylpropane. What was the ratio of bromomethane to 2-bromo-2-methylpropane in the mixture?
Chapter 13 Solutions
Organic Chemistry (9th Edition)
Ch. 13.5A - In a 300-MHz spectrometer, the protons in...Ch. 13.5B - Prob. 13.2PCh. 13.6 - Determine the number of different kinds of protons...Ch. 13.6 - Prob. 13.4PCh. 13.7 - Draw the integral trace expected for the NMR...Ch. 13.7 - Prob. 13.6PCh. 13.8C - Draw the NMR spectra you would expect for the...Ch. 13.8D - Draw the NMR spectra you expect for the following...Ch. 13.8D - a. Assign protons to the peaks in the NMR spectrum...Ch. 13.8D - Prob. 13.10P
Ch. 13.8D - Two spectra are shown. Propose a structure that...Ch. 13.9 - Prob. 13.12PCh. 13.9 - The spectrum of trans-hex-2-enoic acid follows. a....Ch. 13.9 - Prob. 13.14PCh. 13.9 - Prob. 13.15PCh. 13.10 - Prob. 13.16PCh. 13.10 - If the imaginary replacement of either of two...Ch. 13.10 - Predict the theoretical number of different NMR...Ch. 13.11B - Prob. 13.19PCh. 13.11B - Prob. 13.20PCh. 13.11B - Prob. 13.21PCh. 13.11B - Prob. 13.22PCh. 13.11B - Prob. 13.23PCh. 13.11B - Prob. 13.24PCh. 13.12E - Draw the expected broadband-decoupled 13 C N M R...Ch. 13.12E - a. Show which carbon atoms correspond with which...Ch. 13.12E - Repeat Problem13-25, sketching the...Ch. 13.12F - Prob. 13.28PCh. 13.13 - A bottle of allyl bromide was found to contain a...Ch. 13.13 - A laboratory student was converting cyclohexanol...Ch. 13.14 - Sets of spectra are given for two compounds. For...Ch. 13 - An unknown compound has the molecular formula C 9...Ch. 13 - Prob. 13.34SPCh. 13 - Predict the approximate chemical shifts of the...Ch. 13 - Prob. 13.36SPCh. 13 - Prob. 13.37SPCh. 13 - Prob. 13.38SPCh. 13 - Prob. 13.39SPCh. 13 - Prob. 13.40SPCh. 13 - For each compound shown below. 1. sketch the 13 C...Ch. 13 - Prob. 13.42SPCh. 13 - Prob. 13.43SPCh. 13 - Prob. 13.44SPCh. 13 - Prob. 13.45SPCh. 13 - Prob. 13.46SPCh. 13 - A compound was isolated as a minor constituent in...Ch. 13 - Prob. 13.48SPCh. 13 - The three isomers of dimethylbenzene are commonly...Ch. 13 - a. Draw all six isomers of formula C 4 H 8...Ch. 13 - Prob. 13.51SPCh. 13 - Hexamethylbenzene undergoes free-radical...Ch. 13 - Each of these four structures has molecular...Ch. 13 - Prob. 13.54SPCh. 13 - Phenyl Grignard reagent adds to 2-methylpropanal...Ch. 13 - Prob. 13.56SP
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
- An oxidation reaction was conducted using cyclohexanol and NaOCl to make cyclohexanone. How can we know that the NMR for cyclohexanone is in fact cyclohexanone( the NMR for cyclohexanone is not labeled). Analyze the spectra to prove its identity along with the NMR of the starting material which is the spectra labeled cyclohexanol below.arrow_forwardCompound CsH12 gives the following H-NMR. Draw the structure of the compound. Draw a box around the structure you want graded. 5.00 1.00 6.04 70 6.5 6.0 4.0 3.5 3.0 25 20 1.5 A student was adding bromine across the double bond of 2-butene to make 2,3-dibromobutane. After taking the NMR, the student discovered they didn't get the product expected. Based on the NMR, what product did they obtain? Draw a box around your answer. 1.00 2.01 |2.00 3.00arrow_forwardShow the proton and carbon NMR peaks. This can be the NMR graph OR a list of peaks labeled 1,2,3 or a, b, c. Label the 1H NMR spectral data (1,2,3 or a, b, c) and match the peaks to ALL the product molecule's H by labeling them (1,2,3 or a, b, c). Show that you know which 1H-NMR peaks correspond to each hydrogen atoms on your molecule. Label the 13C NMR spectral data (1,2,3 or a, b, c) and match the peaks to ALL the product molecule's C by labeling them (1,2,3 or a, b, c). Show that you know which 13C NMR peaks correspond to each hydrogen atoms on your molecule. - Ph IZ OH MeO Mearrow_forward
- Find how many peaks will appear in the proton (1H) NMR spectrum and carbon (13C) NMR spectrum of each molecue. Don't take into account splitting in the proton(1H) NMRarrow_forwardAssign 1H NMR chemical shifts (ppm values) to the hydrogens indicated in the structure below (see Expt. #4 for the spectrum). Place your answers in the spaces provided next to the structure.arrow_forwardDraw the structure of the compound identified by the simulated 'H NMR and ¹3C NMR spectra. The molecular formula of the compound is C₁0H₁2O. (Blue numbers next to the lines in the 'H NMR spectra indicate the integration values.) ¹H NMR 1H 2H 2H 2H 2H 3H IT 111 10 8 6 8 (ppm) 13C NMR III. 220 200 180 160 140 60 40 20 100 8 (ppm) Deduce the structure from the spectra. Select Draw More CHO 2 Ć Rings 120 80 Erase Q 2 Qarrow_forward
- Steps in Spectral Identification: •Identify major peaks in IR spectrum, if any. •Deduce structural fragments for each of the 1H NMR spectral signals. •Give the structure of the compound •Assign the signals in the 1H NMR spectra to specific protons •Assign carbons to the peaks in the 13C NMR spectrum Step 1. Calculate the degree of unsaturation for the unknown. Step 2. Determine the functional group from IR Step 3. Analyzing the MS spectrum Step 4. Analyzing the 1H NMR spectra Determine the number of different kinds of protons Step 5. Analyzing the 13C NMR spectraarrow_forwardThere are four isomers shown below (compounds A-D). TWO of these isomeric nitrogen- containing compounds were extracted and isolated from tobacco leaves. Their structures were determined using 1H NMR. These two 1H NMR spectra are shown below. Make peak assignments of the NON-AROMATIC signals to determine which TWO isomers are represented. Use the specific labels (a-h) provided with spectra.arrow_forwardThe NMR spectrum of 3-nitroaniline was taken in deuterated dimethylsulfoxide (DMSO), not CDCl3. Why? a) The residual CHCl3 peak would get in the way of the aromatic peaks in the product.b) 3-Nitroaniline is not soluble in CDCl3.c) DMSO allows visualization of the peaks for the NH2 group.d) 3-Nitrobenzamide is not soluble in CDCl3.arrow_forward
- Following is a 1H-NMR spectrum of 2-butanol. Explain why the CH2 protons appear as a complex multiplet rather than as a simple quintet.arrow_forwardPlease 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_forwardI have an NMR spectrum. There are 5 peaks. There is a doublet at 9.6 ppm (integrates to 2H) where aldehydes usually arise, don't know why there is a doublet. There is another doublet at 6.8 ppm, again integrating to 2H. There is a singlet at 4.5 ppm, integrating to 1H. There is a quartet at 3.4 ppm integrating to 2H, and lastly there is triplet at 1.2 ppm integrating to 3H. i recofnize the ethyl group but don't understand the peak at 9.6 unless it is not an aldehyde.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY