EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 13.8, Problem 15P
3-Bromo-1-phenyl-1-propene shows a complex NMR spectrum in which the vinylic proton at C2 is coupled with both the C1 vinylic proton (J = 16 Hz) and the C3 methylene protons (J = 8 Hz). Draw a tree diagram for the C2 proton signal, and account for the fact that a five-line multiplet is observed.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
At an electrified interface according to the Gouy-Chapman model, what types of interactions do NOT occur between the ions and the solvent according to this theory?
Please predict the products for each of the
following reactions.
Clearly show the regiochemistry (Markovnikov
vs anti-Markovnikov) and stereochemistry
(syn- vs anti- or both).
If a mixture of enantiomers is formed, please
draw all the enantiomers.
Hint: In this case you must choose the best
answer to demonstrate the stereochemistry of
H2 addition.
1.03
2. (CH3)2S
BIZ
CH₂OH
2. DMS
KMnO4, NaOH
ΖΗ
Pd or Pt (catalyst)
HBr
20 1
HBr
ROOR (peroxide)
HO
H-SO
HC
12 11 10
BH, THE
2. H2O2, NaOH
Brz
cold
HI
19
18
17
16
MCPBA
15
14
13
A
Br
H₂O
BH3⚫THF
Brz
EtOH
Pd or Ni (catalyst)
D₂ (deuterium)
1. Os04
2. H2O2
CH3CO3H
(peroxyacid)
1. MCPBA
2. H₂O*
H
B
+
H
H
H
"H
C
H
H
D
Explain how Beer’s Law can be used to determine the concentration in a selected food sample. Provide examples.
Chapter 13 Solutions
EBK 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
- Explain the importance of having a sampling plan with respect to food analysis. Explain the importance of having a sampling plan with respect to food analysis. Provide examples.arrow_forwardPlease predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. cold KMnO4, NaOH 2. DMS 1. 03 CH3OH Br2 1. 03 2. (CH3)2S H₂ Pd or Pt (catalyst) HBr 18 19 20 1 HBr ROOR (peroxide) H₂O H₂SO4 HCI HI 17 16 6 15 MCPBA 1. BH3 THF 2. H₂O2, NaOH 1. OsO4 2. H₂O₂ 110 CH3CO₂H (peroxyacid) 1. MCPBA 2. H₂O* Br2 H₂O BH3 THF B12 EtOH Pd or Ni (catalyst) D₂ (deuterium) Bra A B C D H OH H OH OH H OH α α α OH H OH OH фон d H "Harrow_forwardBriefly indicate the models that describe the structure of the interface: Helmholtz-Perrin, Gouy-Chapman, Stern and Grahame models.arrow_forward
- Using Benzene as starting materid show how each of the Following molecules Contel Ve syntheswed CHI 9. b -50311 с CHY 503H Ночто d. อ •NOV e 11-0-650 NO2arrow_forwardThe molecule PYRIDINE, 6th electrons and is therefore aromatre and is Assigned the Following structure contering Since aromatk moleculoy undergo electrophilic anomatic substitution, Pyridine shodd undergo The Following reaction + HNO3 12504 a. write all of the possible Mononitration Products that could Result From this reaction 18. Bared upon the reaction mechanison determime which of these producty would be the major Product of the hegetionarrow_forwarda. Explain Why electron withdrawing groups tend to be meta-Directors. Your answer Should lyclude all apropriate. Resonance contributing Structures fo. Explain why -ll is an outho -tura drccton even though chlorine has a very High Electronegativityarrow_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
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY