EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 14, Problem 51P
How can 1H NMR distinguish between the compounds in each of the following pairs?
Expert Solution & Answer
Learn your wayIncludes step-by-step video
schedule18:08
Students have asked these similar questions
How can 1H NMR distinguish between the compounds in the following pairs?
Compound A has molecular formula C7H7X. Its ¹H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at
6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C-
NMR shows five signals. The mass spectrum of A shows a peak at m/z 170 and another peak at m/z = 172; the relative
height of the two peaks is 1:1 respectively.
- Identify what atom X is, explaining your reasoning
- Identify Compound A, explaining your reasoning
Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The ¹H-NMR spectrum of B
shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass
spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1
respectively.
- Identify compound B, explaining your reasoning
Compound B is treated with sodium ethoxide to generate compound C. The ¹H-NMR spectrum of C shows…
How would you use NMR to distinguish between this pair
of compounds?
Chapter 14 Solutions
EBK ORGANIC CHEMISTRY
Ch. 14.1 - Prob. 1PCh. 14.1 - Prob. 2PCh. 14.4 - How many signals would you expect to see in the 1H...Ch. 14.4 - How many signals would you expect to see in the 1H...Ch. 14.4 - How could you distinguish the 1H NMR spectra of...Ch. 14.4 - Draw an isomer of dichlorocyclopropane that gives...Ch. 14.5 - Prob. 7PCh. 14.5 - Prob. 8PCh. 14.5 - Prob. 9PCh. 14.5 - Where would you expect to find the 1H NMR signal...
Ch. 14.6 - Prob. 11PCh. 14.7 - Prob. 12PCh. 14.7 - Prob. 13PCh. 14.7 - Without referring to Table 14.1, label the proton...Ch. 14.8 - [18]-Annulene shows two signals in its 1H NMR...Ch. 14.9 - How would integration distinguish the 1H NMR...Ch. 14.9 - Which of the following compounds is responsible...Ch. 14.10 - Prob. 19PCh. 14.10 - Explain how the following compounds, each with the...Ch. 14.10 - The 1H NMR spectra of two carboxylic acids with...Ch. 14.11 - Draw a diagram like the one shown in Figure 14.12...Ch. 14.12 - Indicate the number of signals and the...Ch. 14.12 - Explain the relative chemical shifts of the...Ch. 14.12 - How can their 1H NMR spectra distinguish the...Ch. 14.12 - Identify each compound from its molecular formula...Ch. 14.12 - Predict the splitting patterns for the signals...Ch. 14.12 - Describe the 1H NMR spectrum you would expect for...Ch. 14.12 - Propose structures that are consistent with the...Ch. 14.13 - Prob. 30PCh. 14.13 - Identify the compound with molecular formula...Ch. 14.14 - Prob. 32PCh. 14.15 - a. For the following compounds, which pairs of...Ch. 14.15 - How would the 1H NMR spectra for the four...Ch. 14.17 - Explain why the chemical shift of the OH proton of...Ch. 14.17 - Prob. 38PCh. 14.17 - Prob. 39PCh. 14.17 - Prob. 40PCh. 14.20 - Answer the following questions for each compound:...Ch. 14.20 - Prob. 42PCh. 14.20 - How can 1,2-, 1,3-, and 1,4-dinitrobenzene be...Ch. 14.20 - Identify each compound below from its molecular...Ch. 14.22 - Prob. 45PCh. 14.22 - What does cross peak X in Figure 14.34 tell you?Ch. 14 - Prob. 47PCh. 14 - Draw a spitting diagram for the Hb proton and give...Ch. 14 - Label each set of chemically equivalent protons,...Ch. 14 - Determine the ratios of the chemically...Ch. 14 - How can 1H NMR distinguish between the compounds...Ch. 14 - Prob. 52PCh. 14 - Match each of the 1H NMR spectra with one of the...Ch. 14 - The 1H NMR spectra of three isomers with molecular...Ch. 14 - Prob. 55PCh. 14 - Prob. 56PCh. 14 - Compound A, with molecular formula C4H9Cl, shows...Ch. 14 - Would it be better to use 1H NMR or 13C NMR...Ch. 14 - There are four esters with molecular formula...Ch. 14 - Identify the compound with molecular formula C6H14...Ch. 14 - An alkyl halide reacts with an alkoxide ion to...Ch. 14 - The 1H NMR spectra of three isomers with molecular...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Prob. 65PCh. 14 - How can the signals in the 6.5 to 8.1 ppm region...Ch. 14 - The 1H NMR spectra of two compounds, each with...Ch. 14 - Draw a splitting diagram for the Hb proton if Jbc...Ch. 14 - Sketch the following spectra that would be...Ch. 14 - How can 1H NMR be used to prove that the addition...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Dr. N. M. Arr was called in to help analyze the 1H...Ch. 14 - Calculate the amount of energy (in calories)...Ch. 14 - The following 1H NMR spectra are four compounds,...Ch. 14 - When compound A (C5H12O) is treated with HBr, it...Ch. 14 - Identity the compound with molecular formula...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Prob. 78PCh. 14 - Identify each of the following compounds from its...
Additional Science Textbook Solutions
Find more solutions based on key concepts
53. This reaction was monitored as a function of time:
A plot of In[A] versus time yields a straight ...
Chemistry: Structure and Properties (2nd Edition)
Determine [OH], [H+], and the pH of each of the following solutions. a. 1.0 M KCl b. 1.0 M KC2H3O2
Chemistry
In the following diagram, the white spheres represent hydrogen atoms and the blue Sphere represent the nitrogen...
Chemistry: The Central Science (13th Edition)
1.3 Obtain a bottle of multivitamins and read the list of ingredients. What are four chemicals from the list?
Chemistry: An Introduction to General, Organic, and Biological Chemistry (12th Edition) - Standalone book
For each of the following molecules, (1) draw the correct Lewis structure; (2) label each polar covalent bond w...
General, Organic, and Biological Chemistry (3rd Edition)
28. Consider the unbalanced equation for the neutralization of acetic acid:
Balance the equation and determine...
Introductory Chemistry (6th Edition)
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 could 1H NMR spectroscopy be used to distinguish between each pair of compounds?arrow_forwardDraw the structure of a compound with the molecular formula C8H₁0 that exhibits five signals in its ¹3C NMR spectrum, four of which appear between 100 and 150 ppm.arrow_forwardThere are four esters with molecular formula C4H8O2. How can they be distinguished by 1H NMR?arrow_forward
- 5) For the following questions draw the structure of the compound based off of the molecular formula and NMR that is given. a) C9H20 b) C10H12O2 brs, 1H t, 12H 9.8H PPM 1,3H d, 2H d, 2H 1q.2H 1,2H Draw the structure of the compound. C₂H20 Draw the structure of the compound. C₁0H1202 PPM c) CH10O3 (compound contains two functional groups with carbonyls) Don't worry about stereochemistry of the product. s, 1H d) CsH8O3 brs, 1H 10 9.1H dt, 1H PPM J=17 Hz DOM 9.2H d, 3H 1,3H Draw the structure of the compound. C7H1003 1,2H Draw the structure of the compound. brs, 1H d, 1H dt, 2H 0 C₂H₂O₂arrow_forwardThe compound whose 1H NMR spectrum is shown has the molecular formula C3H6Br2. Propose a structure.arrow_forwardCompound A has molecular formula C7H7X. Its 1H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C-NMR shows five signals. The mass spectrum of A shows a peak at m/z = 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The 1H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoning Compound B is treated with sodium ethoxide to generate compound C. The 1H-NMR spectrum of C shows…arrow_forward
- What is the structure of an unknown compound with molecular formula C6H15N that gives the following 1H NMR absorptions: 0.9 (singlet, 1 H), 1.10 (triplet, 3 H), 1.15 (singlet, 9 H), and 2.6 (quartet, 2 H) ppm?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_forwardIdentify the structures of isomers A and B (molecular formula C8H9Br).arrow_forward
- What is the structure of the compound with the formula C8H10O, that shows six signals in its 13C-NMR spectrum, The 1H-NMR spectrum is: 1.98 ppm (1H singlet) 2.82 ppm (2H triplet) 3.80 ppm (2H triplet) 7.22 ppm (5H broad multiplet)arrow_forwardHow many 1H NMR signals does attached compound show ?arrow_forwardA compound with molecular formula C3H8O produces a broad signal between 3200 and 3600 cm1 in its IR spectrum and produces two signals in its 1°C NMR spectrum. Draw the structure of the compound.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY