Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 13, Problem 13.53SP
Each of these four structures has molecular formula C4cH8O2. Match the structure with its characteristic proton NMR signals. (Not all of the signals are listed in each case.)
- a. sharp 1H singlet at δ 8.0 and 2H triplet at δ 4.0
- b. sharp 3H singlet at δ 2.0 and 2H quartet at δ 4.1
- c. sharp 3H singlet at δ 3.7 and 2H quartet at δ 2.3
- d. broad 1H singlet at δ 11.5 and 2H triplet at δ 2.3
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Construct a structure of the given 1H NMR data signals.A.
C4H11N
0.94 δ (3H, triplet)
1.50 δ (2H, sextet)
1.69 δ (1H, singlet)
2.40 δ (3H, singlet)
2.55 δ (2H, triplet)
B.
C9H11Br
2.15 δ (2H, quintet, J = 7 Hz)
2.75 δ (2H, triplet, J = 7 Hz)
3.38 δ (2H, triplet, J = 7 Hz)
7.22 δ (5H, multiplet)
1Compound 1 has molecular formula C7H16. It shows three signals in the 1H-NMR spectrum, one at 0.85 ppm, one at 1.02 ppm, and one at 1.62 ppm. The relative integrals of these three signals are 6, 1, and 1, respectively.
Compound 2 has molecular formula C7H14. It shows three signals in the 1H-NMR spectrum, one at 0.98 ppm, one at 1.36 ppm, and one at 1.55 ppm. The relative integrals of these three signals are 3, 2, and 2, respectively.
Propose structures for compounds 1 and 2, explaining how you reach your conclusion.
The compound G's 1H-NMR spectrum is shown below. Assign the spectrum (feel free to
just use arrows from the chemical structure drawing to the spectrum signals).
.N*
9
8
7
6
5
4
3
PPM
-2
Assign the 13C-NMR spectrum for the compound G above (feel free to just use arrows
from the chemical structure drawing to the spectrum signals).
кадж
180
160
140
120
100
PPM
80
60
40
20
-0
Chapter 13 Solutions
Organic Chemistry (9th Edition)
Ch. 13.5A - In a 300-MHz spectrometer, the protons in...Ch. 13.5B - Prob. 13.2PCh. 13.6 - Determine the number of different kinds of protons...Ch. 13.6 - Prob. 13.4PCh. 13.7 - Draw the integral trace expected for the NMR...Ch. 13.7 - Prob. 13.6PCh. 13.8C - Draw the NMR spectra you would expect for the...Ch. 13.8D - Draw the NMR spectra you expect for the following...Ch. 13.8D - a. Assign protons to the peaks in the NMR spectrum...Ch. 13.8D - Prob. 13.10P
Ch. 13.8D - Two spectra are shown. Propose a structure that...Ch. 13.9 - Prob. 13.12PCh. 13.9 - The spectrum of trans-hex-2-enoic acid follows. a....Ch. 13.9 - Prob. 13.14PCh. 13.9 - Prob. 13.15PCh. 13.10 - Prob. 13.16PCh. 13.10 - If the imaginary replacement of either of two...Ch. 13.10 - Predict the theoretical number of different NMR...Ch. 13.11B - Prob. 13.19PCh. 13.11B - Prob. 13.20PCh. 13.11B - Prob. 13.21PCh. 13.11B - Prob. 13.22PCh. 13.11B - Prob. 13.23PCh. 13.11B - Prob. 13.24PCh. 13.12E - Draw the expected broadband-decoupled 13 C N M R...Ch. 13.12E - a. Show which carbon atoms correspond with which...Ch. 13.12E - Repeat Problem13-25, sketching the...Ch. 13.12F - Prob. 13.28PCh. 13.13 - A bottle of allyl bromide was found to contain a...Ch. 13.13 - A laboratory student was converting cyclohexanol...Ch. 13.14 - Sets of spectra are given for two compounds. For...Ch. 13 - An unknown compound has the molecular formula C 9...Ch. 13 - Prob. 13.34SPCh. 13 - Predict the approximate chemical shifts of the...Ch. 13 - Prob. 13.36SPCh. 13 - Prob. 13.37SPCh. 13 - Prob. 13.38SPCh. 13 - Prob. 13.39SPCh. 13 - Prob. 13.40SPCh. 13 - For each compound shown below. 1. sketch the 13 C...Ch. 13 - Prob. 13.42SPCh. 13 - Prob. 13.43SPCh. 13 - Prob. 13.44SPCh. 13 - Prob. 13.45SPCh. 13 - Prob. 13.46SPCh. 13 - A compound was isolated as a minor constituent in...Ch. 13 - Prob. 13.48SPCh. 13 - The three isomers of dimethylbenzene are commonly...Ch. 13 - a. Draw all six isomers of formula C 4 H 8...Ch. 13 - Prob. 13.51SPCh. 13 - Hexamethylbenzene undergoes free-radical...Ch. 13 - Each of these four structures has molecular...Ch. 13 - Prob. 13.54SPCh. 13 - Phenyl Grignard reagent adds to 2-methylpropanal...Ch. 13 - Prob. 13.56SP
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- Compound 1 has molecular formula C7H16. It shows three signals in the 1H-NMR spectrum, one at 0.85 ppm, one at 1.02 ppm, and one at 1.62 ppm. The relative integrals of these three signals are 6, 1, and 1, respectively. Compound 2 has molecular formula C7H14. It shows three signals in the 1H-NMR spectrum, one at 0.98 ppm, one at 1.36 ppm, and one at 1.55 ppm. The relative integrals of these three signals are 3, 2, and 2, respectively. Propose structures for compounds 1 and 2, explaining how you reach your conclusion.arrow_forward16. A compound with molecular formula CsH,1002 has the following 'H NMR spectrum: Proton NMR 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 모 6.33 Integration Values 19.4 37.9 Determine the number of protons giving rise to each signal.arrow_forwardThe 13C NMR spectra (decoupled 13C 1H spectrum and 3 DEPT spectra) and 1H NMR spectra of the compound in CDC13are shown below. Its molecular formula is C6H1002. Explain why the answer to this spectrum is this molecule -3495.6 1D Carbon DEPT45 ամուր DEPT90 DEPT135 www 200 7.0 1.0 18866 Loave 6.5 -3474.9 3473.2 7.0 180 -3459.3 6.0 elllle ppm 1.0 160 5.5 - 2922.2 2920.5 02162 5.9 wanando 5.0 140 ма 4.5 2906.6 2904.9 2903.2 2901.5 2.0 B 120 4.0 100 f1 (ppm) 3.5 3.0 2091.3 2084.2 2077.1 2069.9 CDCI 3 80 2.5 2.0 60 1.5 6879 933.6 3.0 926.7 924.9 5.8 ppm 4.2 ppm Figure 2: ¹H NMR spectra recorded in CDC13. 3.0 1.9 40 ppm ppm سال I 20 L 0 *** 1.3 ppmarrow_forward
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