Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 14, Problem 48P
Assuming that the force constant is approximately the same for C–C, C–N, and C–O bonds, predict the relative positions of their stretching vibrations in an IR spectrum.
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Rank the following bonds in terms of their expected vibrational frequencies
F-H, C-H, O-H, N-H
What is the order of decreasing vibrational frequency for C — Cl, C — Br, C — C, C — O and C — H ?
From each pair, predict which bond will have the higher vibrational frequency?
a) C–N and C–P b) C=C and C–C
Chapter 14 Solutions
Organic Chemistry
Ch. 14.1 - Which of the following fragments produced in a...Ch. 14.2 - What distinguishes the mass spectrum of...Ch. 14.2 - What is the most likely m/z value for the base...Ch. 14.3 - Prob. 5PCh. 14.3 - If a compound has a molecular ion with an...Ch. 14.3 - a. Suggest possible molecular formulas for a...Ch. 14.3 - Identify the hydrocarbon that has a molecular ion...Ch. 14.4 - Predict the relative intensities of the molecular...Ch. 14.5 - Which molecular formula has an exact molecular...Ch. 14.5 - Prob. 11P
Ch. 14.6 - Sketch the mass spectrum expected for...Ch. 14.6 - The mass spectra of 1-methoxybutane,...Ch. 14.6 - Prob. 14PCh. 14.6 - Identify the ketones responsible for the mass...Ch. 14.6 - Prob. 16PCh. 14.6 - Using curved arrows, show the principal fragments...Ch. 14.6 - The reaction of (Z)-2-pentene with water and a...Ch. 14.9 - Prob. 19PCh. 14.9 - Prob. 20PCh. 14.9 - Prob. 21PCh. 14.13 - Prob. 22PCh. 14.14 - Which occur at a larger wavenumber: a. the C O...Ch. 14.14 - Prob. 24PCh. 14.14 - Prob. 25PCh. 14.14 - Rank the following compounds from highest...Ch. 14.14 - Which shows an O H stretch at a larger...Ch. 14.15 - Prob. 28PCh. 14.15 - a. An oxygen-containing compound shows an...Ch. 14.15 - Prob. 30PCh. 14.15 - For each of the following pair of compounds, name...Ch. 14.16 - Which of the following compounds has a vibration...Ch. 14.16 - Prob. 33PCh. 14.17 - A compound with molecular formula C4H6O gives the...Ch. 14.19 - Prob. 35PCh. 14.19 - Prob. 36PCh. 14.20 - Predict the max of the following compound:Ch. 14.20 - Prob. 38PCh. 14.21 - a. At pH = 7 one of the ions shown here is purple...Ch. 14.21 - Prob. 40PCh. 14.22 - Prob. 41PCh. 14.22 - Prob. 42PCh. 14 - In the mass spectrum of the following compounds,...Ch. 14 - Prob. 44PCh. 14 - For each of the following pairs of compounds,...Ch. 14 - Draw structures for a saturated hydrocarbon that...Ch. 14 - a. How could you use IR spectroscopy to determine...Ch. 14 - Assuming that the force constant is approximately...Ch. 14 - In the following boxes, list the types of bonds...Ch. 14 - A mass spectrum shows significant peaks at m/z. =...Ch. 14 - Prob. 51PCh. 14 - Prob. 52PCh. 14 - Prob. 53PCh. 14 - How can you use UV spectroscopy to distinguish...Ch. 14 - Rank the following compounds from highest...Ch. 14 - Rank the following compounds from highest...Ch. 14 - What peaks in their mass spectra can be used to...Ch. 14 - Each of the IR spectra shown below is accompanied...Ch. 14 - Prob. 59PCh. 14 - Prob. 60PCh. 14 - How can IR spectroscopy distinguish between...Ch. 14 - 62. Draw the structure of a carboxylic acid that...Ch. 14 - Prob. 63PCh. 14 - Give approximate wavenumbers for the major...Ch. 14 - Prob. 65PCh. 14 - Prob. 66PCh. 14 - Prob. 67PCh. 14 - The IR spectrum of a compound with molecular...Ch. 14 - Which one of the following live compounds produced...Ch. 14 - Prob. 70PCh. 14 - Phenolphthalein is an acid-base indicator. In...Ch. 14 - Which one of the following five compounds produced...Ch. 14 - The IR and mass spectra for three different...
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- Payalarrow_forwardIf the spacings between adjacent vibrational features in a photoelectron spectroscopy experiment decrease, changing by a factor of 1/2, when you deuterate the molecule being ionized, is it more likely that the orbital from which you are ejecting an electron is from a nonbonding orbital, a p orbital localized on a C-C or C-O bond, or a s orbital localized on a C-H bond? Explain.arrow_forwardCalculate the number of possible vibrational modes for each of the following molecules and assign frequency ranges to each. i) NH3 ii) C2H4 iii) CCl2F2 iv) CH3CH2OH b) Which of the above molecules will absorb IR radiations most strongly? Explain your answer.arrow_forward
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- Indicate whether each statement is true or false. The larger the number of atoms in a molecule, the more degrees of freedom of rotational and vibrational motion it likely has.arrow_forwardThe force constant for the bond in CO is 1857 N/m, Calculate the vibrational frequencies (in Hz) of 12C160, 13C160, 12C180, and 13C180. Use integer relative masses for this estimate.arrow_forwardWhich of the following bonds would you expect to have the largest frequency of vibration? Α) 1Η-1Η Β) 2Η-2Η C) 1H-79Br D) 1H-12C Ε) 12C-16Οarrow_forward
- Which of the following statements about vibrational frequencies are true? (There is more than one correct answer.) Choice 1 of 3:A. A vibrational frequency corresponds to an internal movement of a molecule, such as a bond lengthening and shortening. Choice 2 of 3:B. An imaginary frequency corresponds to a molecular movement downhill from a saddle point. Choice 3 of 3:C. All molecular structures have at least one imaginary frequency.arrow_forwardConsider the following statements as they apply to infrared spectroscopy. Decide if each is true or false. True False The quantized nature of molecular vibrations are generally understood in terms of a rigid rotor model. True False Absorption bands in infrared spectroscopy are due to vibrational and rotational-vibrational transitions in molecules. True False For a given pair of atoms, the vibrational frequency expected if they are joined by a single bond should be higher than if they are joined by a double bond. True False Because molecules in condensed phases (solids and liquid) are not free to rotate, rotational-vibrational transitions are not observed in their infrared spectra. For this reason, even at high resolution, a condensed phase spectrum is characterized by broad bands. True False Heteronuclear diatomic molecules such as HCl do not absorb infrared radiation.arrow_forwardMatch the region of the electromanetic spectrum with the type of chemical spectroscopy. Nuclear magnetic resonance (NMR) - electron and proton resonance Options: X-rays Microwaves Infared Radio waves Ultraviolet and visible light Raman spectroscopy-molecular rotations options: X-rays Microwaves Infared Radio waves Ultraviolet and visible light Electron excitation (energy level changes) Options: X-rays Microwaves Infared Radio waves Ultraviolet and visible light IR spectroscopy - molecular vibrations Options: X-rays Microwaves Infared Radio waves Ultraviolet and visible light Ionization Options: X-rays Microwaves Infared Radio waves Ultraviolet and visible lightarrow_forward
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