Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 14, Problem 14.60P
Identify the structures of isomers E and F (molecular formula
each signal.
a. Compound E:IR absorption at
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Identify the structures of isomers E and F (molecular formula C4H8O2). Relative areas are given above each signal.
a.Compound E: IR absorption at 1743 cm−1b.Compound F: IR absorption at 1730 cm−1
Identify the structures of isomers E and F (molecular formula C4H8O2).Relative areas are given above each signal.a.) Compound E: IR absorption at 1743 cm−1
b.) Compound F: IR absorption at 1730 cm−1
1Compound 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.
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...
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- When measured on a spectrometer operating at 200 MHz, chloroform (CHCl3) shows a single sharp absorption at 7.3 δ. (a) How many parts per million downfield from TMS does chloroform absorb? (b) How many hertz downfield from TMS would chloroform absorb if the measurement were carried out on a spectrometer operating at 360 MHz? (c) What would be the position of the chloroform absorption in δ units when measured on a 360 MHz spectrometer?arrow_forwardFollowing are two constitutional isomers with the molecular formula C4H8O2. (a) Predict the number of signals in the 1H-NMR spectrum of each isomer. (b) Predict the ratio of areas of the signals in each spectrum. (c) Show how you can distinguish between these isomers on the basis of chemical shift.arrow_forwardThe following 1H NMR peaks were recorded on a spectrometer operating at 200 MHz. Convert each into δ units. (a) CHCl3; 1454 Hz (b) CH3Cl; 610 Hz (c) CH3OH; 693 Hz (d) CH2Cl2; 1060 Hzarrow_forward
- The 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_forward3-Bromo-1-phenyl-1-propene shows a complex NMR spectrum in which the vinylic proton at C2 is coupled with both the C1 vinylic proton (J = 16 Hz) and the C3 methylene protons (J = 8 Hz). Draw a tree diagram for the C2 proton signal, and account for the fact that a five-line multiplet is observed.arrow_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 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 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.arrow_forward14. 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.arrow_forward
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