Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 12, Problem 12.30SP
Interpretation Introduction
Interpretation: Each given structure with its characteristic absorption in the IR is to be matched.
Concept introduction: An IR spectrum is a graph for the energy absorbed by a molecule as a function of the frequency or
To determine: The each given structure with its characteristic absorption in the IR.
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Identify all the peaks from the IR spectrum. Be sure to list the cm-1 and the bond that corresponds to each peak.
For each set of spectral data below, draw the skeletal structure of the molecule that is consistent with the data.
a. C5H12OMajor IR peaks: 3000 -2850 cm-11H NMR: 1.10 ppm (doublet); 3.60 ppm (septet), 3.8 ppm (quartet), 1.05 ppm (triplet)
b. C3H6Br2Major IR peaks: 3000 -2850 cm-11H NMR: 2.4 ppm (quintet) and 3.5 ppm (triplet)
Calculate the IHD and identify the important peaks in the following MS spectral data and draw the structure of the important peaks in the following MS spectral data.
Chapter 12 Solutions
Organic Chemistry (9th Edition)
Ch. 12.3 - Complete the following conversion table. (cm1)...Ch. 12.5 - Which of the bonds shown in red are expected to...Ch. 12.7C - For each hydrocarbon spectrum, determine whether...Ch. 12.9A - Spectra are given for three compounds. Each...Ch. 12.10 - The infrared spectra for three compounds are...Ch. 12.12 - Prob. 12.6PCh. 12.14B - Identify which of these four mass spectra indicate...Ch. 12.15A - Show the fragmentation that accounts for the...Ch. 12.15A - Show the fragmentations that give rise to the...Ch. 12.15B - Ethers are not easily differentiated by their...
Ch. 12.15C - Prob. 12.11PCh. 12 - Prob. 12.12SPCh. 12 - Prob. 12.13SPCh. 12 - All of the following compounds absorb infrared...Ch. 12 - Prob. 12.15SPCh. 12 - Four infrared spectra are shown, corresponding to...Ch. 12 - Predict the masses and the structures of the most...Ch. 12 - Prob. 12.18SPCh. 12 - Prob. 12.19SPCh. 12 - (A true story) While organizing the undergraduate...Ch. 12 - Prob. 12.21SPCh. 12 - Prob. 12.22SPCh. 12 - An unknown, foul-smelling hydrocarbon gives the...Ch. 12 - covered a synthesis of alkynes by a double...Ch. 12 - Three IR spectra are shown, corresponding to three...Ch. 12 - Prob. 12.26SPCh. 12 - Prob. 12.27SPCh. 12 - Prob. 12.28SPCh. 12 - The ultimate test of fluency in MS and IR is...Ch. 12 - Prob. 12.30SPCh. 12 - Consider the following four structures, followed...
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- Propose a structure consistent with each set of data.a.) C9H10O2: IR absorption at 1718 cm−1 b.) C9H12: IR absorption at 2850–3150 cm−1arrow_forwardComplete the table with 3 Major IR peaks. IR Peak, cm-1 Bond Typearrow_forwarda. An oxygen-containing compound shows an absorption band at ~1700 cm-1 and no absorption bands at ~3300 cm-1, ~2700 cm-1, or ~1100 cm-1. What class of compound is it? b. A nitrogen-containing compound shows no absorption band at ~3400 cm-1 and no absorption bands between ~1700 cm-1 and ~1600 cm-1 or between 2260 cm-1 and 2220 cm-1. What class of compound is it?arrow_forward
- A. Below is a “Name Reaction” - Clemensen reduction. Describe how the IR spectrum could be used to tell if the reactions had been successful. Provide approximate wave numbers and the corresponding functional groups for the key absorption bands and/or peaks in IR. You might want to describe from two aspects: which peak(s) of what functional group(s) should appear in the IR of the product (that is different from the reactant); which peak(s) of what functional group(s) should disappear in the IR of the product (that is present in the reactant B. For the Clemensen reduction (same reaction), describe how the 1H NMR spectrum could be used to tell if the reactions had been successful. Provide approximate chemical shifts and the integral and the “splitting” of the “unique” in the NMR spectrum. You might want to describe from two aspects: which peak(s) should have a change in chemical shift(s); which peak(s) should have a change in integral; which has a splitting change; which peak(s) will be…arrow_forwardWhat are the important diagnostic peaks in this IR spectra? Fingerprint region <1500cm^-1 is not necessary. Thank you.arrow_forward1. An aliphatic ketone absorbs at 1,715 cm-1. What is the frequency of this vibration in hertz, which is cycles per second or just per second, reciprocal seconds? 2. What is the energy equivalent of this stretching vibration in kcal/mole? 3. Why does 3,4-diethyl-3-hexene not have a carbon to carbon double bond stretching absorption band? 4. Why does a carbon to oxygen double bond absorption band have a greater intensity than a carbon to carbon double bond absorption band? 5. Using only IR, explain in detail how one could most easily differentiate between oct-1-ene and oct-1-yne if all carbon to carbon bonds are ignored. 6. Using only IR, explain in detail how one could most easily differentiate between butan-1-ol and butanoic acid.arrow_forward
- Name the major IR absorptions and write the name of the unknown compound and its structure.arrow_forwardHow many signals are greater than 100 ppm in the 13C NMR? How many signals are less than 100 ppm in the 13C NMR? How many signals total in the 13C NMR?arrow_forwardProvide structures that are consistent with the attached DEPT spectra (A-C). Each set of spectra includes a DEPT-90 (top), DEPT-135 (middle) and standard 13C decoupled spectrum (bottom). a) C5H11Brarrow_forward
- Explain IR spectroscopy of the following output from one experiment:arrow_forwardWhen performing the oxidation reaction, what absorptions would you expect to see in the product that are not present in the starting material? How could you tell by IT spectral analysis that the reaction went to completion (no starting material remains)?arrow_forwardIdentify as many peaks as possible. This is the IR Spectroscopy of an unknown solid in Nujol.arrow_forward
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