Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 15, Problem 62P
Identity each of the following compounds from its molecular formula and its 1R and 1H NMR spectra:
- a. C5H12O
- b. C6H12O2
- c. C4H7ClO2
- d. C4H8O2
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Q2: Ranking Acidity
a) Rank the labeled protons in the following molecule in order of increasing pKa. Briefly
explain the ranking. Use Table 2.2 as reference.
Ha
Нь
HC
H-N
Ha
OHe
b) Atenolol is a drug used to treat high blood pressure. Which of the indicated N-H bonds is
more acidic? Explain. (Hint: use resonance structures to help)
Name the functional groups on atenolol.
H
H-N
atenolol
Ν
H-N
OH Н
Answer d, e, and f
If the rotational constant of a molecule is B = 120 cm-1, it can be stated that the transition from 2←1:a) gives rise to a line at 120 cm-1b) is a forbidden transitionc) gives rise to a line at 240 cm-1d) gives rise to a line at 480 cm-1
Chapter 15 Solutions
Organic Chemistry
Ch. 15.1 - Prob. 1PCh. 15.1 - Prob. 2PCh. 15.4 - How many signals would you expect to see in the 1H...Ch. 15.4 - Prob. 4PCh. 15.4 - How could you distinguish the 1H NMR spectra of...Ch. 15.4 - Draw an isomer of dichlorocyclopropane that gives...Ch. 15.5 - Prob. 7PCh. 15.5 - Prob. 8PCh. 15.5 - Prob. 9PCh. 15.5 - Where would you expect to find the 1H NMR signal...
Ch. 15.6 - Prob. 11PCh. 15.7 - Prob. 12PCh. 15.7 - Prob. 13PCh. 15.7 - Without referring to Table 14.1, label the proton...Ch. 15.8 - [18]-Annulene shows two signals in its 1H NMR...Ch. 15.9 - How would integration distinguish the 1H NMR...Ch. 15.9 - Which of the following compounds is responsible...Ch. 15.10 - Prob. 19PCh. 15.10 - Explain how the following compounds, each with the...Ch. 15.10 - The 1H NMR spectra of two carboxylic acids with...Ch. 15.11 - Draw a diagram like the one shown in Figure 14.12...Ch. 15.12 - Indicate the number of signals and the...Ch. 15.12 - How can their 1H NMR spectra distinguish the...Ch. 15.12 - Identify each compound from its molecular formula...Ch. 15.12 - Prob. 27PCh. 15.12 - Propose structures that are consistent with the...Ch. 15.12 - Describe the 1H NMR spectrum you would expect for...Ch. 15.13 - Prob. 30PCh. 15.13 - Identify the compound with molecular formula...Ch. 15.14 - Prob. 32PCh. 15.15 - a. For the following compounds, which pairs of...Ch. 15.17 - Explain why the chemical shift of the OH proton of...Ch. 15.17 - Prob. 37PCh. 15.17 - Prob. 38PCh. 15.17 - Prob. 39PCh. 15.20 - Answer the following questions for each compound:...Ch. 15.20 - Prob. 41PCh. 15.20 - How can 1,2-, 1,3-, and 1,4-dinitrobenzene be...Ch. 15.20 - Identify each compound below from its molecular...Ch. 15.22 - Prob. 44PCh. 15.22 - What does cross peak X in Figure 14.34 tell you?Ch. 15 - Prob. 46PCh. 15 - Draw a spitting diagram for the Hb proton and give...Ch. 15 - Label each set of chemically equivalent protons,...Ch. 15 - Match each of the 1H NMR spectra with one of the...Ch. 15 - Determine the ratios of the chemically...Ch. 15 - How can 1H NMR distinguish between the compounds...Ch. 15 - Prob. 52PCh. 15 - The 1H NMR spectra of three isomers with molecular...Ch. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Compound A, with molecular formula C4H9Cl, shows...Ch. 15 - The 1H NMR spectra of three isomers with molecular...Ch. 15 - Would it be better to use 1H NMR or 13C NMR...Ch. 15 - There are four esters with molecular formula...Ch. 15 - An alkyl halide reacts with an alkoxide ion to...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Prob. 64PCh. 15 - How can the signals in the 6.5 to 8.1 ppm region...Ch. 15 - The 1H NMR spectra of two compounds, each with...Ch. 15 - Draw a splitting diagram for the Hb proton if Jbc...Ch. 15 - Sketch the following spectra that would be...Ch. 15 - How can 1H NMR be used to prove that the addition...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Dr. N. M. Arr was called in to help analyze the 1H...Ch. 15 - Calculate the amount of energy (in calories)...Ch. 15 - The following 1H NMR spectra are four compounds,...Ch. 15 - When compound A (C5H12O) is treated with HBr, it...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Identify each of the following compounds from its...Ch. 15 - Identity the compound with molecular formula...Ch. 15 - Identify the compound with molecular formula C6H14...
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