Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 14, Problem 14.31P
A compound of molecular formula
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
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.
The 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d
= 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the
-3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula
C7H6O2. Draw structures for compounds A and B.
A ¹H NMR spectrum is shown for a molecule with the molecular
formula of C10H12O4. Draw the structure that best fits this data.
1H
11
10
2H
2H
U
7
1H
1H
ΤΗ 1Η
ppm
Q
Chapter 14 Solutions
Organic Chemistry
Ch. 14 - Problem 14.1 The NMR spectrum of recorded on a ...Ch. 14 - Prob. 14.2PCh. 14 - How many 1H NMR signals does each compound show?Ch. 14 - How many 1H NMR signals does each...Ch. 14 - Label the protons in each highlighted CH2 group as...Ch. 14 - How many 1H NMR signals would you expect for each...Ch. 14 - Prob. 14.7PCh. 14 - For each compound, first label each different type...Ch. 14 - Prob. 14.9PCh. 14 - Which compound give a 1H NMR spectrum with two...
Ch. 14 - Prob. 14.11PCh. 14 - Prob. 14.12PCh. 14 - Prob. 14.13PCh. 14 - For each compound give the number of 1H NMR...Ch. 14 - Prob. 14.15PCh. 14 - Prob. 14.16PCh. 14 - Describe the 1H NMR spectrum of each compound....Ch. 14 - Draw a splitting diagram for Hb in...Ch. 14 - Problem 14.20 Identify A and B, isomers of...Ch. 14 - Problem 14.21 How many signals are present in the ...Ch. 14 - What protons in alcohol A give rise to each signal...Ch. 14 - How many peaks are observed in the NMR signal for...Ch. 14 - Propose a structure for a compound of molecular...Ch. 14 - Problem 14.25 Propose a structure for a compound...Ch. 14 - Problem 14.26. Identify products A and B from the...Ch. 14 - How many lines are observed in the 13C NMR...Ch. 14 - Problem 14.28 Draw all constitutional isomers of...Ch. 14 - Esters of chrysanthemic acid are naturally...Ch. 14 - Prob. 14.29PCh. 14 - Problem 14.31 Identify the carbon atoms that give...Ch. 14 - Problem 14.32 A compound of molecular formula ...Ch. 14 - Problem 14.33 Draw the structure of a compound of...Ch. 14 - 14.34 (a) How many NMR signals does each of the...Ch. 14 - 14.35 (a) How many NMR signals does each compound...Ch. 14 - How many different types of protons are present in...Ch. 14 - How many 1H NMR signals does each compound give?...Ch. 14 - 14.37 How many NMR signals does each natural...Ch. 14 - Prob. 14.38PCh. 14 - Acetone exhibits a singlet in its 1H NMR spectrum...Ch. 14 - Prob. 14.40PCh. 14 - Prob. 14.41PCh. 14 - How could you use chemical shift and integration...Ch. 14 - Which compounds give one singlet in the 1H NMR...Ch. 14 - Prob. 14.44PCh. 14 - 14.43 How can you use NMR spectroscopy to...Ch. 14 - Prob. 14.46PCh. 14 - Prob. 14.47PCh. 14 - Which compounds in Problem 14.43 give one signal...Ch. 14 - Prob. 14.49PCh. 14 - How many 13C NMR signals does each compound...Ch. 14 - Rank the highlighted carbon atoms in each compound...Ch. 14 - 14.50 Identify the carbon atoms that give rise to...Ch. 14 - 14.51 a. How many signals does dimethyl...Ch. 14 - 14.53 Propose a structure consistent with each set...Ch. 14 - 14.54 Identify the structures of isomers A and B...Ch. 14 - 14.55 Reaction of with affords compound W,...Ch. 14 - 14.56 Treatment of with , followed by aqueous
...Ch. 14 - 14.57 Compound C has a molecular ion in its mass...Ch. 14 - 14.58 As we will learn in Chapter 20, reaction of ...Ch. 14 - 14.59 Identify the structures of isomers E and F...Ch. 14 - 14.59 Identify the structures of isomers H and I...Ch. 14 - 14.61 Propose a structure consistent with each set...Ch. 14 - 14.62 Reaction of with , followed by treatment...Ch. 14 - Reaction of aldehyde D with amino alcohol E in the...Ch. 14 - 14.64 Propose a structure consistent with each set...Ch. 14 - 14.65 In the presence of a small amount of acid, a...Ch. 14 - 14.66 Treatment of with affords two products (M...Ch. 14 - 14.67 Compound O has molecular formula and shows...Ch. 14 - 14.68 Compound P has molecular formula . Deduce...Ch. 14 - 14.69 Treatment of with strong base followed by ...Ch. 14 - Low molecular weight esters RCO2R often have...Ch. 14 - 14.70 When -bromo--dimethylbutane is treated with...Ch. 14 - 14.71 Propose a structure consistent with each set...Ch. 14 - 14.72 Reaction of unknown A with forms...Ch. 14 - Prob. 14.75PCh. 14 - 14.74 -Annulene shows two signals in its ...Ch. 14 - 14.75 Explain why the spectrum of-methylbutan--ol...Ch. 14 - 14.76 Because has an odd mass number, nuclei...Ch. 14 - 14.77 Cyclohex--enone has two protons on its...
Additional Science Textbook Solutions
Find more solutions based on key concepts
The smallest building blocks inside your cell phone are about 1000 times smaller than the diameter of a human h...
Chemistry In Context
45. Calculate the mass of nitrogen dissolved at room temperature in an 80.0-L home aquarium. Assume a total pre...
Chemistry: Structure and Properties
4. 38 Strontium has four naturally occurring isotopes, with mass numbers 84, 86, 87, arid 88.
a. Write the atom...
Basic Chemistry (5th Edition)
4.1 Write the symbols for the following elements.
a. copper
b. platinum
c. calcium
d. manganese
e. Iron
...
Chemistry: An Introduction to General, Organic, and Biological Chemistry (13th Edition)
The active ingredient in Tylenol and a host of other over-the-counter pain relievers is acetaminophen (C8H9NO2)...
Chemistry: Atoms First
22.102 Write the structures of the cis and tram isomers, if any, for the following compounds:
Chemistry: The Molecular Nature of Matter
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
- The 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_forwardThe 1H and 13C NMR spectra of compound A, C8H9Br, are shown. Propose a structure for A, and assign peaks in the spectra to your structure.arrow_forwardPropose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forward
- How could you use 1H NMR, 13C NMR, and IR spectroscopy to help you distinguish between the following structures?arrow_forwardHow would you use NMR (either 13C or 1H) to distinguish between the following pairs of isomers?arrow_forwardGive and explain the analysis of H-NMR and C-NMR spectra of the followingarrow_forward
- 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 PPMarrow_forwardA compound with molecular formula C3H8O produces a broad signal between 3200 and 3600 cm³¹ in its IR spectrum and produces two signals in its 13C NMR spectrum. Draw the structure of the compound. Draw Your Solutionarrow_forwardDraw the structure of the compound identified by the simulated 'H NMR and 13C NMR spectra. The molecular formula of the compound is C1,H120. (Blue numbers next to the lines in the 'H NMR spectra indicate the integration values.) Η NMR 1H 2H 2H 2H 2H 3H| 10 8 4 2 8 (ppm) 13C NMR 220 200 180 160 140 120 100 80 60 40 20 d (ppm)arrow_forward
- A compound with a molecular formula of C8H₁6O has the following 'H NMR spectrum. Provide a structure that is consistent with this spectrum. y سد سلما ش A PPM B с Darrow_forward13. Which compound has four distinct signals in its 13C NMR spectrum? أن لا يا بنا I II III IV Br Varrow_forwardConsider the 'C NMR spectrum below for the given compound. 220 200 180 160 140 120 100 80 60 40 40 ppm Highlight the carbon(s) corresponding to the labeled peak. OH 20 х 0arrow_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