Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 12, Problem 12.25SP
Three IR spectra are shown, corresponding to three of the following compounds. For each spectrum, determine the structure and explain how the peaks in the spectrum correspond to the structure you have chosen.
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4.) Determine and draw the structure corresponding to the spectral information provided below. As you make this determination, complete the table below. Explain what clues you used to determine the structure.
The 1H and 13C NMR for a compound with the formula C5H12O are shown. Determine the structure of this compound. Assign the peaks: assign “a” to the most shielded hydrogen(s) in your structure, “b” to next-most shielded, etc; use capital letters for carbons).
Based on the spectra provided, draw the structure. Label each unique carbon and hydrogen with the letters A, B, C… for use in assigning NMR peaks. fill in the data table assigning peaks in each spectrum. You should assign:
• All 1H NMR peaks (do not worry about the peaks for CDCl3 at 7.26 ppm or the peak for TMS at 0 ppm)
• Significant IR peaks above 1600 cm
Example of what the table should include (imagine the structure of ethanol is drawn with the CH3 hydrogens labeled as A, the CH2 hydrogens labeled as B, and the OH hydrogen labeled as C) :
hydrogen
proton chemical shift
integration
splitting pattern
couples to..
A
1.2
3
triplet
B
B
3.7
2
quartet
A
C
2.6
1
singlet
-
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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Practice Problem ATTEMPT
Write the rate expressions for each of the following reactions:
(a)
(b)
(c)
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- The 1H and 13C NMR spectra of compound A, C8H9Br, are shown. Propose a structure for A, and assign peaks in the spectra to your structure.arrow_forwardDetermine the molecular structure of the compound in the IR spectrum data, 1H NMR ; 13C NMR and MS, explain it for each picture.arrow_forwardChoose the molecule to which this IR spectrum corresponds.arrow_forward
- The H1H1 NMR spectrum shown corresponds to an unknown compound with the molecular formula C6H10C6H10. There are no strong IR bands between 2100 and 2300 or 3250 and 3350 cm−1. Deduce and draw the structure of the molecule that corresponds to the spectrum.arrow_forwardThe following NMR spectra were obtained from a compound with the molecular formula C4H6O. Use this information to predict its structure.arrow_forwardList ALL the significant peaks in the IR spectrum of each molecule below by showing which functional group should have an absorbance at which wave number. They might have more than one functional grouparrow_forward
- Based on the spectra provided, draw the structure. Label each unique carbon and hydrogen with the letters A, B, C… for use in assigning NMR peaks. fill in the data table assigning peaks in each spectrum. You should assign: • All 1H NMR peaks • Significant IR peaks above 1600 cm Example of what the table should include (imagine the structure of ethanol is drawn with the CH3 hydrogens labeled as A, the CH2 hydrogens labeled as B, and the OH hydrogen labeled as C) : hydrogen proton chemical shift integration splitting pattern couples to.. A 1.2 3 triplet B B 3.7 2 quartet A C 2.6 1 singlet -arrow_forwardCalculate the IHD of C7H6XNO 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.arrow_forwardWhich of the following molecules is responsible for this IR spectrum?arrow_forward
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