EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 12, Problem 12.6P
Interpretation Introduction
Interpretation:
The peak corresponding to the stretching frequency of
Concept introduction:
Wavelength is the distance between the two crests or troughs of the wave. It is denoted by the symbol
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The infrared absorbtion of the N-H stretch in amines occurs approximately at
a wavelength of 2.9 x 10-6 m. What is the approximate vibrational force
constant, k, of N-H bond?
Note: you can assume the reduced mass is equal to the mass of the H atom
(which is reasonable since it's attached to a much heavier atom).
48.0 kg/s?
1.20 x 102 kg/s2
7.0 x 102 kg/s2
4.2 x 10-1 kg/s?
1.3 x 103 kg/s?
13C NMR spectroscopy provides valuable information about the environments of a molecule's carbon atoms. Since carbon atoms are often connected to hydrogen atoms, which could split the carbon signal through spin-spin coupling, the coupling between C and H is often "turned off" through the use of broadband decoupling, causing each C signal to appear as a singlet.
Draw an isomer of C5H11Cl that would be expected to have four resonances in its 13C NMR spectra.
7. Consider the C=O stretching data for the following cyclic ketones: cyclopropane 1813 cm³¹; cyclobutanone
1791 cm³¹; cyclopentanone 1740 cm³¹.
(a) which ketone has the strongest bond?
(b) where in the trend would you expect the C=O stretch of cyclopropenone? (Use the hybridization information
in the same way we used hybridization for C-H stretching.)
Chapter 12 Solutions
EBK ORGANIC CHEMISTRY
Ch. 12 - Prob. 12.1PCh. 12 - Prob. 12.2PCh. 12 - Prob. 12.3PCh. 12 - Prob. 12.4PCh. 12 - Prob. 12.5PCh. 12 - Prob. 12.6PCh. 12 - Prob. 12.7PCh. 12 - Prob. 12.8PCh. 12 - Prob. 12.9PCh. 12 - Prob. 12.10P
Ch. 12 - Prob. 12.11PCh. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Prob. 12.14PCh. 12 - Prob. 12.15PCh. 12 - Prob. 12.16PCh. 12 - Prob. 12.17PCh. 12 - Prob. 12.18PCh. 12 - Prob. 12.19PCh. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Prob. 12.22PCh. 12 - Prob. 12.23APCh. 12 - Prob. 12.24APCh. 12 - Prob. 12.25APCh. 12 - Prob. 12.26APCh. 12 - Prob. 12.27APCh. 12 - Prob. 12.28APCh. 12 - Prob. 12.29APCh. 12 - Prob. 12.30APCh. 12 - Prob. 12.31APCh. 12 - Prob. 12.32APCh. 12 - Prob. 12.33APCh. 12 - Prob. 12.34APCh. 12 - Prob. 12.35APCh. 12 - Prob. 12.36APCh. 12 - Prob. 12.37APCh. 12 - Prob. 12.38APCh. 12 - Prob. 12.39APCh. 12 - Prob. 12.40APCh. 12 - Prob. 12.41APCh. 12 - Prob. 12.42APCh. 12 - Prob. 12.43APCh. 12 - Prob. 12.44AP
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- Norlutin and Enovid are ketones that suppress ovulation, so they have been used clinically as contraceptives. For which of these compounds would you expect the infrared carbonyl absorption (C=O stretch) to be at a higher frequency? Explain.arrow_forward4. Why does a carbon to oxygen double bond absorption band have a greater intensity than a carbon to carbon double bond absorption band?arrow_forward3. 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.arrow_forward
- An infrared spectrum of a mixture of methyl amine, CH3−NH2, and methylene imine, CH2=NH2, displayed absorptions at 1050 and 1640 cm−1cm−1, among others. Which of these two absorptions would you expect belongs to the C−N and which to the C=N stretch?arrow_forwardA student has acquired an IR spectra of an unknown six-carbon molecule and has determined that it is either 2-hexyne, 1- hexyne, or 1-hexene. How can the student use their knowledge of IR spectroscopy to determine the identity of the molecule? In your answer, clearly specify what regions of the IR spectrum the student should look at and what bonds are responsible for the absorption bands you indicate.arrow_forwardCalculate the energy in KJ/mol associated with the 3.517-μm vibrational absorption bandof an aliphatic ketone.arrow_forward
- Why do aldehydes, esters, and amides all have a strong absorption in the 1630-1780 cm1 region of their IR spectra? A) The bond between H and the sp³-hybridized C in these functional groups vibrates in this energy range. B) Each of these functional groups has at least two resonance structures, and the different vibrations of the resonance structures give off energy in this region. C) The bond between O and the sp²-hybridized C in these functional groups vibrates at a frequency in this energy range. D) Light at this wavenumber causes the average C to O bond length to increase which causes more of this light to be transmitted. E) An electron in the bond of these functional groups gets excited to the * orbital.arrow_forwardHow do the following factors affect absorption frequencies? O-H vs O-D. CH stretch, hybrid orbitals used by carbonarrow_forwardThe beer-lambert law is A = εlc, where A is the absorbance, ε is the molar extinction coefficient, l is the path lengh in cm and C is the concentration. The beer lambert law can be expressed in the form of y=mx + b, where A is y, and C is x.What is b and how is it used to calculate the final absorbance?arrow_forward
- What IR frequencies would enable a chemist to distinguish between these molecules? CH;CH2OH and CH;CH2OCH;CH3 and CH, HCHCHCCIICH CH, d 3000-3100 cm-1 (=C-H)| 1620-1680 cm-1 (C=C) 3200-3400 cm-1 (OH) || 3000-3100 cm-1 (=C-H)arrow_forwardThe infrared absorption spectrum of 12C14N has its strongest band at 2500 cm-1 wavenumber. Calculate the force constant (N/m) of the bond in this molecule.arrow_forwardConvert the following infrared wavelengths to cm-1. (a) 6.24 mm, typical for an aromatic C=C (b) 3.38 mm, typical for a saturated C¬H bondarrow_forward
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IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY