ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 14, Problem 14.32P
A compound of molecular formula
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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 NMR signals does each compound show?
a....Ch. 14 - How many 1H NMR signals does each...Ch. 14 - How many 1H NMR signals does each compound give?...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. 14.8PCh. 14 - For each compound, first label each different type...Ch. 14 - Label each statement as True or False. a. When a...
Ch. 14 - Prob. 14.11PCh. 14 - Problem 14.12 Which compound give a NMR spectrum...Ch. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - For each compound give the number of 1H NMR...Ch. 14 - Prob. 14.16PCh. 14 - Prob. 14.17PCh. 14 - Problem 14.18 Describe the NMR spectrum of each...Ch. 14 - Problem 14.19 Draw a splitting diagram for 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 - Problem 14.22 What protons in alcohol A give rise...Ch. 14 - How many peaks are observed in the NMR signal for...Ch. 14 -
Problem 14.24 Propose a structure for a compound...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 - Problem 14.27 How many lines are observed in the ...Ch. 14 - Problem 14.28 Draw all constitutional isomers of...Ch. 14 - Problem 14.29 Esters of chrysanthemic acid are...Ch. 14 - Prob. 14.30PCh. 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 - Prob. 14.36PCh. 14 - 14.37 How many NMR signals does each natural...Ch. 14 - Prob. 14.38PCh. 14 - 14.39 What effect does increasing the operating...Ch. 14 - Prob. 14.40PCh. 14 - 14.41 How could you use chemical shift and...Ch. 14 - Prob. 14.42PCh. 14 - 14.43 How can you use NMR spectroscopy to...Ch. 14 - Prob. 14.44PCh. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - Prob. 14.47PCh. 14 - 14.48 How many NMR signals does each compound...Ch. 14 - 14.49 Rank the highlighted carbon atoms in each...Ch. 14 - 14.50 Identify the carbon atoms that give rise to...Ch. 14 - 14.51 a. How many signals does dimethyl...Ch. 14 - 14.52 Answer the following questions about each of...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 - 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. 14.73PCh. 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...
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- 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
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- 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
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