Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Question
Chapter 14.15, Problem 28P
Interpretation Introduction
Interpretation:
The way to analyse the absorption band at
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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
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A (µm)
2.5
100
8 9 10 11 12 13 14 15
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Frequency (cm¬!)
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(%) Transmission
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.
A 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.
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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