Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 10, Problem 52P
For each of the following pairs of compounds, identify one IR absorption band that could be used to distinguish between them:
- a. CH3CH2CH2OH and CH3CH2OCH3
- b. CH3CH2CH = CHCH3 and CH3CH2C − CCH3
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2
2. Compound B has a molecular formula of CHH2O It has a characteristic IR signal at
around 1700 cm. Draw the molecular structure of B.
3H
2H 2H
2H
1H
1H 1H
5
PPM
3
200
180
160
140
120
100
80
60
40
PPM
CH3
c=C
H3C
H.
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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- 2. Compound B has a molecular formula of C₁H₁2O₂. It has a characteristic IR signal at around 1700 cm³¹. Draw the molecular structure of B. 3H 1H 1H 1H L 200 180 160 140 PPM 120 PPM 100 2H 2H 80 60 2H 40 20arrow_forwardA compound is known to be one of those shown here. What absorption bands in its IR spectrum allow you to identify the compound?arrow_forwarda) what bond is present in ketones but not alkanes? b) what is the wavenumber range of the signals that are present in the diagnostic region of all of the ketone IR spectra (but not the alkanes)? c) is the new band strong or weak compared with a C=C or a C≡C stretch?arrow_forward
- Identify the structures of isomers H and I (molecular formula C8H11N).a.Compound H: IR absorptions at 3365, 3284, 3026, 2932, 1603, and 1497 cm−1b.Compound I: IR absorptions at 3367, 3286, 3027, 2962, 1604, and 1492 cm−1arrow_forward15) Which compound does not have a strong, characteristic IR absorption near 1700 cm-1? B) (CH3CH2)20 C) CH3CH2CHO D) (CH3CH2)2C=Oarrow_forwardFor each of the following pairs of compounds, identify one IR absorption band that could be used to distinguish between them:arrow_forward
- What IR absorption would you use to distinguish between the two compounds below? a CH3CCH₂CH3 O 2850-2960 1715 3400-3650 O2210-2260 A and CH3 b CH3CHCH₂CH3arrow_forwardThese are the 1H spectrums for compounds Y and Z (molecular formula on the image). They both show a stretch around 1710cm-1 on the IR spectrum. What are the structures for both Y and Z?arrow_forwardUse the 1H NMR and IR data to determine the structure of each compound.arrow_forward
- Identify the structures of isomers H and I (molecular formula C&HuN). a. Compound H: IR absorptions at 3365, 3284, 3026, 2932, 1603, and 1497 cm 2H 5 H 2H 2H 0 2 3 4 5 6 7 ppm b. Compound I: IR absorptions at 3367, 3286, 3027, 2962, 1604, and 1492 cm1 3 H 5 H 1 H 2 H 3 2 8 5 4 7arrow_forwardChemistry Amide groups have a uniquely low-energy C=O stretch; it can be easily observed by IR spectroscopy. Which of the following amide C=O stretches has the higher absorption value in wavenumbers (cm ¹) and why? NO₂ ly so 'N 1 2 2 because the CO double bond is weaker 2 because the CO double bond is stronger 1 because the CO double bond is weaker 1 because the CO double bond is strongerarrow_forwardSelect the bond in each molecule that would be expected to have the strongest IR absorption. Select only one type of bond in each molecule. If there are multiples of one bond type for a molecule, select them all. Do not highlight atoms.arrow_forward
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