Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 13, Problem 13.41SP
For each compound shown below.
- 1. sketch the 13 C N M R spectrum (totally decoupled, with a singlet for each type of carbon), showing approximate chemical shifts.
- 2. show the multiplicity expected for each signal in the off-resonance-decoupled spectrum.
- 3. sketch the spectra expected using the DEPT-90 and DEPT-135 techniques.
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Identify likely groups and identify likely signals on the IR. (ex. OH, NH, C=C, C-H sp3, aromatic etc)
Construct a simulated proton-decoupled 13C NMR spectrum for tert-butylamine. Drag the resonance signal
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if there were no proton decoupling.
CH3
NH₂
H3C
t
S
q
³1³
140
200
120
220
100
80
60
40
20
0
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180
160
Identify all the peaks in the H-NMR and C-NMR spectrum. Record the chemical shift, the splitting, and the number of hydrogens for each peak in the NMR table.
Please fill in the data similar to the example table down below.
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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- Following is the mass spectrum of an unknown compound. The two highest peaks are at m/z 120 and 122. Suggest a structure for this compound. (Data from http://webbook.nist.gov/chemistry/.)arrow_forwardWhat fragments might you expect in the mass spectra of the following compounds?arrow_forwardMolar mass: 120 Label the major peaks in each spectrum and propose a structure for the compound.arrow_forward
- 4. Determine the multiplicity and predict the chemical shifts of each signal in the expected 'H NMR spectrum of the following compound. II II IVarrow_forwardCarbon NMR The Decoupled (FC ) spectrum is represented below. Assign every Carbon to its respective chemical shift providing proper analysis. The Carbons are labeled from a to 1 to 5. What signal would you expect to see in DEPT 135/90 and coupled carbon NMR for each carbon 5 CH C-0-CH,-CH3 ь а 3| d CDCI,arrow_forwardQuestion Completion Status: QUESTION 2 Match the hydrogens on the structure below to the appropriate signals and splitting C. N NH он 1. 1.59 ppm, m, 2H va 2. 5.46 ppm, s, 2H 3. 1.31 ppm, sextet, 2H 4. 2.87 ppm, t, 2H 5. 7.29-7.33 ppm, m, 4H ve 6. 0.90 ppm, t, 3H vf 7. 3.65 ppm, br, 1H 8. 7.85 ppm, d, 2H vh 9. 4.73 ppm, s, 2H 10.7.47 ppm, d, 2H QUESTION 3 Would H1 NMR be able to distinguish between the compounds below? Why or why not (Be s Click Save and Submit to save and submit. Click Save All Answers to save all answers.arrow_forward
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