Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 15, Problem 55P
You have a sample of a compound of molecular formula
by two groups,
benzene isomer corresponds to these
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
You have a sample of a compound of molecular formula C11H15NO2, which has a benzene ring substituted by two groups, (CH3)2N− and −CO2CH2CH3, and exhibits the given 13C NMR. What disubstituted benzene isomer corresponds to these 13C data?
14. Compound B has molecular formula C9H12. It shows five signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.22 ppm, a septet of integral 1 at 2.86 ppm, a singlet of integral 1 at 5.34 ppm, a doublet of integral 2 at 6.70 ppm, and a doublet of integral 2 at 7.03 ppm. The 13C-NMR spectrum of B shows six unique signals (23.9, 34.0, 115.7, 128.7, 148.9, and 157.4). Identify B and explain your reasoning.
A compound with the molecular formula C4H₁1N has the following ¹H NMR spectrum, in which the relative integration values are
illustrated with step curves. Which of the following is the correct number of protons giving rise to each signal?
al
O2H, 3H, 6H
Ο 1Η, 4Η, 6Η
O 2H, 4H, 5H
O 3H, 4H, 5H
PPM
Chapter 15 Solutions
Organic Chemistry (6th Edition)
Ch. 15.2 - Prob. 1PCh. 15.2 - Problem 17.2 What orbitals are used to form the...Ch. 15.3 - Prob. 4PCh. 15.3 - Problem-17.5 What is the structure of propofol,...Ch. 15.6 - Prob. 7PCh. 15.8 - Prob. 8PCh. 15.8 - Prob. 11PCh. 15.8 - Prob. 12PCh. 15.8 - Problem 17.16 Rank the following compounds in...Ch. 15.8 - Problem 17.17 Draw the seven resonance structures...
Ch. 15 - 17.23 Name each compound and state how many lines...Ch. 15 - Prob. 21PCh. 15 - Prob. 22PCh. 15 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 15 - 17.28 Draw a structure corresponding to each...Ch. 15 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - 17.38
How many electrons does C contain?
How...Ch. 15 - Prob. 36PCh. 15 - 17.40 Explain the observed rate of reactivity of...Ch. 15 - 17.41 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 39PCh. 15 - 17.43 Draw additional resonance structures for...Ch. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - 17.46 Which compound in each pair is the stronger...Ch. 15 - 17.47 Treatment of indene with forms its...Ch. 15 - Prob. 45PCh. 15 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 15 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 15 - Prob. 48PCh. 15 - Prob. 49PCh. 15 - 17.53 How many signals does each compound...Ch. 15 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 15 - 17.55 Propose a structure consistent with each...Ch. 15 - 17.56 Propose a structure consistent with each...Ch. 15 - 17.57 Thymol (molecular formula ) is the major...Ch. 15 - 17.58 You have a sample of a compound of molecular...Ch. 15 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 15 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 15 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 15 - 17.62 Answer the following questions about...Ch. 15 - 17.63 Stanozolol is an anabolic steroid that...Ch. 15 - Prob. 61P
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
- How would you use NMR (either 13C or 1H) to distinguish between the following pairs of isomers?arrow_forwardThe 13C-NMR spectrum of 3-methyl-2-butanol shows signals at 17.88 (CH3), 18.16 (CH3), 20.01 (CH3), 35.04 (carbon-3), and 72.75 (carbon-2). Account for the fact that each methyl group in this molecule gives a different signal.arrow_forwardPropose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forward
- 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.arrow_forward3. Consider the isomers A, B and C given below: CH3 CH3 CH3 Br A Br Br 2-Bromomethylbenzene 3-Bromomethylbenzene 4-Bromomethylbenzene (a) For each compound how many chemically different proton signals would you expect to see in their 'H NMR spectra? A = В - C = (b) For each proton signal identified above use the m+1 rule to determine the splitting pattern that will be observed for each proton signal of each isomer: doublet ÇH3 CH3 CH3 Br H. H Br H. H. Br A Вarrow_forwardWhich one of these four compounds would give a 13C NMR spectrum with only these three peaks, one at 210, one at 40 and one at 20? H3C OB OD 13C NMR delta (8) values C=O of ketones, aldehydes C=O of acids, esters, amides C=C and C=N C-X (where X = halogen, O) base position, alkyl C OC A OA CH3 H3C B CH3 H3C1 220-200 160-180 100-150 40-70 0 - 40 CH3 H₂C D CH3arrow_forward
- A'H NMR spectrum is shown for a molecule with the molecular formula of CeH9Br. Draw the structure that best fits this data.arrow_forwardA 13C NMR spectrum is shown for a molecule with the molecular formula of C5H10O2. Draw the structure that best fits this data. 180 160 140 120 100 80 60 40 20 PPMarrow_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
- How many signal(s) will appear in the H-NMR spectrum of toluene (structure shown below)? O5 4arrow_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_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
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY