Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 10, Problem 60P
List the following compounds in order from highest wavenumber to lowest wavenumber for their C − O absorption bands:
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Rank each of the bonds identified in order of increasing wavenumber.
1
H
2
0
>
3
Increasing wavenumber
4
>
- OH
5
>
-H
6
7
N
Suppose that hydrogen is replaced by deuterium in1 H35CI. Would you expect the J = 1 ~ 0 transition to move tohigher or lower wavenumber?
3. Identify C-Cl stretching peaks in CDC13 and CHC13 spectra. Do these peaks
have exactly the same frequencies for both compounds? Explain your answer.
4. Is the C==O stretching frequency the same for acetone and deuterated acetone?
Explain your answer.
5. Identify C==O overtone in acetone spectrum which corresponds to the transition
from ground level, n=0, to the second excited level, n=2.
Chapter 10 Solutions
Essential Organic Chemistry, Global Edition
Ch. 10.1 - Prob. 1PCh. 10.2 - What would distinguish the mass spectrum of...Ch. 10.2 - Prob. 3PCh. 10.3 - Prob. 5PCh. 10.3 - Suggest possible molecular formulas for a compound...Ch. 10.3 - Prob. 7PCh. 10.4 - Prob. 8PCh. 10.4 - Prob. 9PCh. 10.5 - Prob. 10PCh. 10.5 - Prob. 11P
Ch. 10.6 - Identify the ketone responsible for the mass...Ch. 10.6 - Prob. 13PCh. 10.8 - Prob. 14PCh. 10.8 - Prob. 15PCh. 10.12 - Which will occur at a larger wavenumber: a. a C :...Ch. 10.13 - Which will occur at a larger wavenumber: a. the C...Ch. 10.13 - Prob. 18PCh. 10.13 - Prob. 19PCh. 10.13 - Which will show an O 8 H stretch at a larger...Ch. 10.14 - Prob. 21PCh. 10.14 - Prob. 22PCh. 10.15 - Prob. 23PCh. 10.15 - Prob. 24PCh. 10.17 - Prob. 25PCh. 10.18 - Prob. 26PCh. 10.18 - Prob. 27PCh. 10.19 - Prob. 28PCh. 10.19 - Prob. 29PCh. 10.22 - How many signals would you expect to see in the 1H...Ch. 10.22 - Prob. 31PCh. 10.22 - Prob. 32PCh. 10.23 - Where would you expect to find the 1H NMR signal...Ch. 10.24 - Prob. 34PCh. 10.25 - Prob. 35PCh. 10.25 - Prob. 36PCh. 10.25 - Prob. 37PCh. 10.26 - Prob. 38PCh. 10.26 - Which of the following compounds is responsible...Ch. 10.27 - Prob. 40PCh. 10.27 - Prob. 41PCh. 10.27 - The 1H NMR spectra of two carboxylic acids with...Ch. 10.28 - Prob. 43PCh. 10.28 - Prob. 44PCh. 10.28 - Prob. 45PCh. 10.28 - Describe the 1H NMR spectrum you would expect for...Ch. 10.28 - Identify the compound with molecular formula...Ch. 10.29 - Prob. 48PCh. 10.29 - Prob. 49PCh. 10.29 - Identify the compound with a molecular formula of...Ch. 10 - In the mass spectrum of the following compounds,...Ch. 10 - For each of the following pairs of compounds,...Ch. 10 - Draw the structure of a saturated hydrocarbon that...Ch. 10 - Prob. 54PCh. 10 - Prob. 55PCh. 10 - How could you use UV spectroscopy to distinguish...Ch. 10 - Prob. 57PCh. 10 - Predict the relative intensities of the molecular...Ch. 10 - Prob. 59PCh. 10 - List the following compounds in order from highest...Ch. 10 - How can 1H NMR be used to prove that the addition...Ch. 10 - There are four esters with molecular formula...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - Each of the IR spectra presented here is...Ch. 10 - Prob. 66PCh. 10 - Five compounds are shown for each of the following...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Phenolphthalein is an acidbase indicator. In...Ch. 10 - Which one of the following five compounds produced...Ch. 10 - Prob. 72PCh. 10 - Prob. 73PCh. 10 - Prob. 74PCh. 10 - How could 1H NMR distinguish between the compounds...Ch. 10 - Prob. 76PCh. 10 - Prob. 77PCh. 10 - The 1H NMR spectra of three isomers with molecular...Ch. 10 - The 1H NMR spectra of three isomers with molecular...Ch. 10 - Identify the following compounds. (Relative...Ch. 10 - An alkyl halide reacts with an alkoxide ion to...Ch. 10 - Determine the structure of a compound with...
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- Propanone (acetone, (CH3)2CO) has a strong absorption at 189 nm and a weaker absorption at 280 nm. Identify the chromophore and assign the absorptions to π* ← n or π* ← π transitions.arrow_forwardWhy is it most accurate to measure absorbances in the range A = 0.3 to 2?arrow_forwardA solution of ethanol has been contaminated with benzene—a technique employed to make ethanol unfit to drink. Benzene has a molar absorptivity of 230 M-1 cm-1 at 260 nm in ethanol, and ethanol shows no absorbance at 260 nm. How can the concentration of benzene in the solution be determined?arrow_forward
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- In the following boxes, list the types of bonds and the approximate wavenumber at which each type of bond is expected to show an IR absorption:arrow_forwardThe 13C NMR spectrum of fluoroethanoic acid shows a multiplet centred at δ = 79. When the same spectrum is recorded using proton decoupling, the multiplet collapses to a doublet with a splitting of 160 Hz. Another multiplet, but with much smaller splittings, is also seen centred at δ =179; this multiplet collapses to a doublet when decoupling is used. Explain these observations.arrow_forward4. NMR: (8 pts) Look at the given molecules and answer the following questions H H Compound A Compound B Compound C OH H Compound D How many different chemical environments (number of peaks) would you expect to see in the 'H NMR for each molecule? A = B = C = D: = Predict how many sub peaks per multiplet would be seen in the signal for the indicated hydrogen due to spin-spin splitting? A = B = C = D = How many H of that particular type (integration) would you expect to see at the indicated hydrogen? A = B = C = D= =arrow_forward
- The IR spectra of nonane (C,H20) and 1-hexanol (C,H13OH) are shown below. Assign each spectrum to the correct compound and identify the frequencies and the functional groups used to support your assignment. λ (μη) 6 7 8 9 10 11 12 1314 15 2.5 100 3 5 20 4 90 80 70 60 50 40 30 20 10 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 Frequency (cm¬') A (µm) 2.5 100 8 9 10 11 12 13 14 15 3 4 5 7 20 90 80 70 60 50 40 30 20 10 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 Frequency (cm¬!) (%) Transmission (%) Transmissionarrow_forwardExplain the Effect of Resonance on IR Absorptions ?arrow_forwardplease don't provide handwritten solutionarrow_forward
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