EBK ORGANIC CHEMISTRY
12th Edition
ISBN: 9781119233664
Author: Snyder
Publisher: VST
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 9, Problem 9PP
PRACTICE PROBLEM 9.9
Propose a structure for compounds A and B whose spectra are shown in Fig. 9.13, and account for the splitting pattern of each signal.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
(a) Compound A has molecular formula C9H18O but shows only one singlet in the 1H-NMR spectrum. Suggest a structure for A and explain your reasoning.
(b) Compound B has molecular formula C10H14. The IR, mass, 1H-NMR, and 13C-NMR speca are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for B and explain your reasoning.
Part 3B Set 2. Can 1H NMR spectroscopy be used to differentiate between the two compounds? Briefly explain why or why not. Predict the 1H NMR spectrum for each compound (include integration, multiplicity, and approximate chemical shift). Either draw the actual spectrum or put in a data table format.
(b) Consider the compound shown below:
How would you expect its 13C NMR spectrum to differ from its non-decoupled 13C NMR spectrum?
Explain your reasoning fully.
Chapter 9 Solutions
EBK ORGANIC CHEMISTRY
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM 9.2 What compound with molecular...Ch. 9 - PRACTICE PROBLEM 9.3
Using the method of Section...Ch. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 8PPCh. 9 - PRACTICE PROBLEM 9.9 Propose a structure for...Ch. 9 - PRACTICE PROBLEM 9.10
What is the dihedral angle...
Ch. 9 - PRACTICE PROBLEM 9.11 Draw the most stable chair...Ch. 9 - Prob. 12PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 14PPCh. 9 - Prob. 15PPCh. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Prob. 19PPCh. 9 - How many 1H NMR signals (not peaks) would you...Ch. 9 - How many 13C NMR signals would you predict for...Ch. 9 - Prob. 22PCh. 9 - Prob. 23PCh. 9 - Prob. 24PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Compound S (C8H16) reacts with one mole of bromine...Ch. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 30PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 32PCh. 9 - Ethyl bromide and methoxybenzene (shown below)...Ch. 9 - 9.34 The homologous series of primary amines, ,...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.36 Propose structures for compounds E and F....Ch. 9 - 9.37 Use the NMR and IR data below to propose a...Ch. 9 - 9.38 When dissolved in , a compound (K) with the...Ch. 9 - Compound T (C5H8O) has a strong IR absorption band...Ch. 9 - Prob. 40PCh. 9 - Deduce the structure of the compound that gives...Ch. 9 - Deduce the structure of the compound that gives...Ch. 9 - The 1H NMR spectrum of a solution of 1,...Ch. 9 - Acetic acid has a mass spectrum showing a...Ch. 9 - The 1H NMR peak for the hydroxyl proton of...Ch. 9 - The 1H NMR study of DMF (N, N-dimethylformamide)...Ch. 9 - 9.48 The mass spectra of many benzene derivatives...Ch. 9 - Prob. 49PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...
Additional Science Textbook Solutions
Find more solutions based on key concepts
The effect of the electron on the shape of the element needs to be explained. Concept introduction: The overall...
Living By Chemistry: First Edition Textbook
3. What are prefix multipliers? List some examples.
Chemistry: Structure and Properties (2nd Edition)
The NF bond is more polar than the NH bond: but NF3 has a smaller dipole moment than NH3. Explain this curious ...
Organic Chemistry (9th Edition)
Freeze concentration is used to produce a fruit-juice concentrate. A stream of fresh juice containing 12 wt% so...
Elementary Principles of Chemical Processes, Binder Ready Version
23. Give the symbol and name for (a) an isotope with a mass number of 37 and an atomic number of 17 and (b) an ...
Chemistry For Changing Times (14th Edition)
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
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
- (c) Each of the following compounds below are characterized by a 'H NMR spectrum that consists of only a single peak having the chemical shift indicated. Identify and draw a bond-line structure for each compound, respectively.. (i) C2H3Cl3-at ~ 2.7 ppm (ii) C5H10-at 1.5 ppmarrow_forward(a) Base on the information provided, determine the structures of compounds. (b) Assign all peaks in 1 H and 13C NMR spectra of compoundsarrow_forward(a) Based on the information provided, determine the structures of compounds. (b) Assign all peaks in 1 H and 13C NMR spectra of compoundsarrow_forward
- Distinguish the characteristics infrared absorption frequencies that would allow you to distinguish the following pair of compounds. (Picture attached)arrow_forwardIII) Can 1H NMR spectroscopy be used to differentiate between the two compounds? Briefly explain why or why not. Predict the 1H NMR spectrum for each compound (include integration, multiplicity, and approximate chemical shift). For each set, be sure that you put them in a data table format!arrow_forwardPart 3B Set 1. Can 1H NMR spectroscopy be used to differentiate between the two compounds? Briefly explain why or why not. Predict the 1H NMR spectrum for each compound (include integration, multiplicity, and approximate chemical shift). Put it in data table format.arrow_forward
- As shows the NMR spectrum of ethanol. Account for the observed chemical shifts.arrow_forward(c) Assign the correct structure for compound M with molecular formula C5H100, which has 'H-NMR signal at 8 = 5-64 (A), 5:53 (B), 4-23 (C), 1-92 (D), (D)is an exchangable singlet (with D20). . multiplets, (Ẹ) and (F) are doublets and a E 1:68 (E) and 1-24 (F)" in рpm. JAR = 16:3 Hz. (A), (B)_ and (C) are (A), TB). and (C) arearrow_forwardThe following is the predicted 1H-NMR spectrum for an unknown compound with molecular formula C6H14O . This compound is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas.arrow_forward
- -1 in its Compound C, C12H18CIN, shows a strong absorption band at 1277 cm IR spectrum. The 'H NMR spectrum for compound C is shown in Figure 3 Deduce the structure of C. Indicate clearly your reasoning involved in developing the proposed structure and include a justification of your signal assignments through explanation of the splitting patterns and chemical shifts observed. Integral = 6 Integral = 4 Integral = 3 Integral = 2 Integral = 2 Integral = 1 6 2 6 (ppm)arrow_forwardYou are given two compounds, dimethylamine (CH3)2NH and ethanamide, CH3CONH2. a) b) c) Which compound is more basic? Explain your answer. How do you distinguish them by infrared spectroscopy? Outline an extraction method to separate a mixture of these two compounds.arrow_forwardHow would infrared spectroscopy be useful in distinguishing between the followingcompounds? Cite absorption bands you would expect from each.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY