ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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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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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.
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)
12.
H₂C
H₂C
1900
4000
CH₂
CH₂ H₂C
CH₂ H₂C
HSP-47-293
3000
3000
NMR Spectrum
ul
CH₂
6
CH3OH
CH₂CH3OH
CH3CEN
Which one of these 17 compounds is represented by this IR and this ¹H NMR
spectrum?
IR Spectrum
тыры
H₂C
2009
2000
CH₂
ppm
H₂C
4
OH
1300
H₂C.
1500
CH₂
O-CH3
1000
OH H₂C
1000
CH₂
o
CH₂
Chapter 13 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
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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