CAREY: ORGANIC CHEMISTRY
10th Edition
ISBN: 9781260364002
Author: VALUE EDITION
Publisher: MCG CUSTOM
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 18, Problem 48P
Interpretation Introduction
Interpretation:
The structure of the isomeric diketones on the basis of the given molecular formula
Concept introduction:
Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and
Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group.
The value of chemical peaks in NMR depends upon the chemical environment around the hydrogen atom.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The 1H-NMR spectrum of compound R, C6H14O, consists of two signals: d 1.1 (doublet) and d 3.6 (septet) in the ratio 6:1. Propose a structural formula for compound R consistent with this information
Compound 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.
The 1H-NMR spectrum of compound B,C7H14O , consists of the following signals: δ 0.9 (t, 6H), 1.6 (sextet, 4H), and 2.4 (t, 4H).
Draw the structural formula of compound B.
Chapter 18 Solutions
CAREY: ORGANIC CHEMISTRY
Ch. 18.1 - Prob. 1PCh. 18.1 - Prob. 2PCh. 18.3 - Prob. 3PCh. 18.4 - Prob. 4PCh. 18.4 - Prob. 5PCh. 18.6 - Prob. 6PCh. 18.7 - Prob. 7PCh. 18.7 - Prob. 8PCh. 18.7 - Prob. 9PCh. 18.8 - Prob. 10P
Ch. 18.8 - Prob. 11PCh. 18.8 - Prob. 12PCh. 18.9 - Prob. 13PCh. 18.10 - Prob. 14PCh. 18.10 - Prob. 15PCh. 18.11 - Problem 18.16 The product of the following...Ch. 18.11 - Prob. 17PCh. 18.12 - Problem 18.18 What other combination of ylide and...Ch. 18.12 - Prob. 19PCh. 18.12 - Prob. 20PCh. 18.12 - Prob. 21PCh. 18.13 - Prob. 22PCh. 18 - (a) Write structural formulas and provide IUPAC...Ch. 18 - Each of the following aldehydes and ketones is...Ch. 18 - The African dwarf crocodile secretes a volatile...Ch. 18 - Prob. 26PCh. 18 - Prob. 27PCh. 18 - Prob. 28PCh. 18 - Prob. 29PCh. 18 - Prob. 30PCh. 18 - Prob. 31PCh. 18 - Each of the following reaction has been reported...Ch. 18 - Prob. 33PCh. 18 - On standing in 17O-labeled water, both...Ch. 18 - Prob. 35PCh. 18 - Prob. 36PCh. 18 - The OH groups at C-4 and C-6 of methyl ...Ch. 18 - Prob. 38PCh. 18 - Prob. 39PCh. 18 - The sex attractant of the female winter moth has...Ch. 18 - Prob. 41PCh. 18 - Prob. 42PCh. 18 - Prob. 43PCh. 18 - Suggest a reasonable mechanism for each of the...Ch. 18 - Prob. 45PCh. 18 - Prob. 46PCh. 18 - Prob. 47PCh. 18 - Prob. 48PCh. 18 - Prob. 49PCh. 18 - Prob. 50PCh. 18 - Prob. 51PCh. 18 - Prob. 52DSPCh. 18 - Prob. 53DSPCh. 18 - Prob. 54DSPCh. 18 - Prob. 55DSPCh. 18 - Prob. 56DSPCh. 18 - Prob. 57DSPCh. 18 - Prob. 58DSP
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
- Following are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. (a) Propose structural formulas of compounds G, H, and I. (b) Explain why there are four lines between 0.86 and 0.90 for compound G. (c) Explain why the 2H multiplets at 1.5 and 3.5 for compound H are so complex.arrow_forwardPropose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra. (a) C5H10O2 (b) C7H14O2 (c) C6 H12O2 (d) C7H12O4 (e) C4H7ClO2 (f) C4H6O2arrow_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_forward
- Compound 2 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. Provide structure for compound 2, explain how you reached your conclusion.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_forwardCompound 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.arrow_forward
- The compound has a molecular formula of C5H10O and the following 13C spectrum. A proton NMR was measured, but the data was lost except for the fact that it showed three distinct signals: a singlet, a doublet, and a septet, all of which appear between 0 and 3 ppm. Identify the compound, and draw its 1H NMR.arrow_forwardFollowing is the 1H-NMR spectrum of compound O, molecular formula C7H12. Compound O reacts with bromine in carbon tetrachloride to give a compound with the molecular formula C7H12Br2. The 13C-NMR spectrum of compound O shows signals at d 150.12, 106.43, 35.44, 28.36, and 26.36. Deduce the structural formula of compound O.arrow_forwardCompound A exhibits two signals in its 1H NMR spectrum at 2.64 and 3.69 ppm and the ratio of the absorbing signals is 2:3. Compound B exhibits two signals in its 1 H NMR spectrum at 2.09 and 4.27 ppm and the ratio of the absorbing signals is 3:2. Which compound corresponds to dimethyl succinate and which compound corresponds to ethylene diacetate?arrow_forward
- identify the compound with molecular formula C2H6O that gives this 1H NMR spectrum.arrow_forwardAn unknown compound, C4H10O gave the following proton NMR data: Singlet at 3.32 ppm (3H) Triplet at 0.94 ppm (3H) Triplet at 3.35 ppm (2H) Multiplet 1.47 ppm (2H) What is the structure of the compound?arrow_forwardIdentify A and B, isomers of molecular formula C3H4Cl2, from the given 1H NMR data: Compound A exhibits peaks at 1.75 (doublet, 3 H, J = 6.9 Hz) and 5.89 (quartet, 1 H, J = 6.9 Hz) ppm. Compound B exhibits peaks at 4.16 (singlet, 2 H), 5.42 (doublet, 1 H, J = 1.9 Hz), and 5.59 (doublet, 1 H, J = 1.9 Hz) ppm.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