Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 13.6, Problem 11P
The integrated 1H NMR spectrum of a compound of formula C4H10O is shown in FIGURE 13-11. Propose a structure.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
The data for four 13C NMR spectra are given below. Match each spectrum with one of the
following structures. Briefly justify your reasoning by labeling each struture.
ÓH
-NH2
А
C
Spectrum 1: 26, 29, 32, 39, 112, 127, 128, 144 ppm
• Spectrum 2: 28, 68 ppm
• Spectrum 3: 12, 23, 33, 70 ppm
• Spectrum 4: 16, 17, 38, 52 ppm
The following ¹H NMR spectrum is shown in two questions.
"nmrsim presentation" 1 1 C:\Bruker TopSpin3.5p17\examdata
10
1,4-Disubstituted benzene ring
Which functional group is BEST attributed to the pair of doublets at about
7-8 ppm, each integrating to 2H?
trans-alkene
Cyclohexene
Carboxylic acid
[ppm]
1,3-Disubstituted benzene ring
[oa]
Compound X of the molecular formula C7H10 has the 13C NMR spectrum (5 signals) shown
below. On treatment with excess H2/Pt (catalytic hydrogenation), X is converted to
methylcyclohexane. Propose a structure for X and justify your reasoning by clearly labeling
each carbon signal and write out the reaction.
200
180
160
140
120
100
80
60
40
20
Chapter 13 Solutions
Organic Chemistry
Ch. 13.1 - Prob. 1PCh. 13.1 - Prob. 2PCh. 13.2 - Prob. 3PCh. 13.3 - The following 1H NMR peaks were recorded on a...Ch. 13.3 - When the 1Η NMR spectrum of acetone, CH3COCH3, is...Ch. 13.4 - Each of the following compounds has a single 1H...Ch. 13.4 - Identify the different types of protons in the...Ch. 13.5 - How many peaks would you expect in the 1H NMR...Ch. 13.6 - Predict the splitting patterns you would expect...Ch. 13.6 - Draw structures for compounds that meet the...
Ch. 13.6 - The integrated 1H NMR spectrum of a compound of...Ch. 13.7 - Identify the indicated sets of protons as...Ch. 13.7 - How many kinds of electronically nonequivalent...Ch. 13.7 - How many absorptions would you expect (S)-malate,...Ch. 13.8 - 3-Bromo-1-phenyl-1-propene shows a complex NMR...Ch. 13.9 - How could you use 1H NMR to determine the...Ch. 13.11 - Prob. 17PCh. 13.11 - Propose structures for compounds that fit the...Ch. 13.11 - Prob. 19PCh. 13.12 - Prob. 20PCh. 13.12 - Prob. 21PCh. 13.12 - Prob. 22PCh. 13.13 - Prob. 23PCh. 13.SE - Into how many peaks would you expect the 1H NMR...Ch. 13.SE - How many absorptions would you expect the...Ch. 13.SE - Sketch what you might expect the 1H and 13C NMR...Ch. 13.SE - How many electronically nonequivalent kinds of...Ch. 13.SE - Identify the indicated protons in the following...Ch. 13.SE - Prob. 29APCh. 13.SE - Prob. 30APCh. 13.SE - When measured on a spectrometer operating at 200...Ch. 13.SE - Prob. 32APCh. 13.SE - Prob. 33APCh. 13.SE - How many types of nonequivalent protons are...Ch. 13.SE - The following compounds all show a single line in...Ch. 13.SE - Prob. 36APCh. 13.SE - Propose structures for compounds with the...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - The acid-catalyzed dehydration of...Ch. 13.SE - How could you use 1H NMR to distinguish between...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Propose structures for the two compounds whose 1H...Ch. 13.SE - Prob. 46APCh. 13.SE - How many absorptions would you expect to observe...Ch. 13.SE - Prob. 48APCh. 13.SE - How could you use 1H and 13C NMR to help...Ch. 13.SE - How could you use 1H NMR, 13C NMR, and IR...Ch. 13.SE - Assign as many resonances as you can to specific...Ch. 13.SE - Assume that you have a compound with the formula...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Long-range coupling between protons more than two...Ch. 13.SE - The 1H and 13C NMR spectra of compound A, C8H9Br,...Ch. 13.SE - Propose structures for the three compounds whose...Ch. 13.SE - The mass spectrum and 13C NMR spectrum of a...Ch. 13.SE - Compound A, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - Propose a structure for compound C, which has...Ch. 13.SE - Prob. 62GPCh. 13.SE - Propose a structure for compound E, C7H12O2, which...Ch. 13.SE - Compound F, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - 3-Methyl-2-butanol has five signals in its 13C NMR...Ch. 13.SE - A 13C NMR spectrum of commercially available...Ch. 13.SE - Carboxylic acids (RCO2H) react with alcohols (ROH)...Ch. 13.SE - Prob. 68GPCh. 13.SE - The proton NMR spectrum is shown for a compound...Ch. 13.SE - The proton NMR spectrum of a compound with the...Ch. 13.SE - The proton NMR spectrum is shown for a compound...
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
- Addition of m-xylene to the strongly acidic solvent HF/SbF5 at 45C gives a new species, which shows 1H-NMR resonances at 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.arrow_forwardFollowing are the 'H and 13C NMR spectra for each of four isomeric bromoalkanes with formula C4H9B.. Assign a structure to each pair of spectra and assign all H's and C's. Carbon spectrum C,H,Br CDCI3 85 80 75 70 65 60 55 50 45 35 30 15 10 5 Proton spectrum D C,H,Br 2.1 2.0 1.9 1.82 0.93 5.37 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0arrow_forwardIndicate two basic differences that exist between the spectra of 1H y 13C in NMR.arrow_forward
- C5H10O2 H Determine H and C Spectra for the compundarrow_forwardPredict the structure of the compound using the information below. Kindly show what information are obtained for each spectra which may help in predicting the structure. From IR Spectra: See the attached picture From Mass Spectra: M+ = 216 peaks at 29 (base peak) and 188 From Proton and Carbon NMR Spectra: See attached picture.arrow_forward(1) ¹H NMR spectrum of an alcohol (C5H12O) is shown with related integral values of the each proton peaks. Propose a structure for this alcohol and assign each protons in this structure. 1H N-> 2 2H elle 8μ (ppm) 6H 3H il 1 0arrow_forward
- Give and explain the analysis of H-NMR and C-NMR spectra of the followingarrow_forwardPlease show work. Compound B has the molecular formula C8H6O2. The IR, 1H-NMR, and 13C-NMR spectra are shown below. Suggest a structure for B and explain your reasoning.arrow_forwardFollowing are the 'H and 13C NMR spectra for each of four isomeric bromoalkanes with formula C4H9B.. Assign a structure to each pair of spectra and assign all H's and C's. Carbon spectrum C,H,Br CDCI3 Proton spectrum C,H,Br В 0.89 1.78 2.59 2.0 1.0arrow_forward
- A molecule of the molecular formula C5H11Br gives rise to the NMR spectrum below. When reacted with NaOH and water, it forms a product which by NMR has 2 protons 1H at 5.4 ppm and 1H at 5.5 ppm each having a 3J coupling of 17 Hz. (other protons also present) The product also has an IR stretch at 1550 cm 1. Provide the structures of the starting material and product. NaOH H,0 C;H„Br 6H triplet 4H quintet 1H quintet 10 8 Ppmarrow_forwardAn unknown compound has the formula C4H12O. Elucidate its structure by scrutinizing its 1H NMR spectra, shown. Specifically, label each different type of H atom in the final structure with its NMR chemical shift in ppm.arrow_forwardDeduce the structure of the compound that gives the following 1H, 13C, and IR spectra. Assign all aspects of the 1H and 13C spectra to the structure you propose. Use letters to correlate protons with the signals in the 1H NMR spectrum, and numbers to correlate carbons with the signals in the 13C spectrum. The mass spectrum of this compound shows the molecular ion at m/z 148. 6H 1H 2H 2H 1H 10 8 6 4 2 84 (ppm) CH CH CH3 CH CH 200 180 160 140 120 100 80 60 40 20 100 90 80 70 60 50 40 30 20 10 4000 3000 2000 1500 1000 500 Wavenumber (cm) Transmittance (%)arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
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
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY