Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 24.SE, Problem 67AP
Draw the structure of the
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Draw the structure of the compound identified by the simulated 'H NMR and 13C NMR spectra.
The molecular formula of the compound is C1,H120.
(Blue numbers next to the lines in the 'H NMR spectra indicate the integration values.)
Η NMR
1H
2H
2H
2H
2H
3H|
10
8
4
2
8 (ppm)
13C NMR
220
200
180
160
140
120
100
80
60
40
20
d (ppm)
A compound with molecular formula C8H8O3 exhibits the following IR, 1H NMR and 13C NMR spectra. Deduce the structure of this compound.
QUESTION 9
Propose a structure for a carboxylic acid with molecular formula C6H10O2 by interpreting the following 13C NMR spectra.
Chapter 24 Solutions
Organic Chemistry
Ch. 24.1 - Name the following compounds:Ch. 24.1 - Prob. 2PCh. 24.1 - Prob. 3PCh. 24.3 - Prob. 4PCh. 24.3 - The benzylammonium ion (C6H5CH2NH3+) has pKa =...Ch. 24.4 - Prob. 6PCh. 24.5 - Prob. 7PCh. 24.6 - Prob. 8PCh. 24.6 - Prob. 9PCh. 24.6 - Show two methods for the synthesis of dopamine, a...
Ch. 24.6 - Prob. 11PCh. 24.6 - Prob. 12PCh. 24.6 - Prob. 13PCh. 24.7 - Prob. 14PCh. 24.7 - Prob. 15PCh. 24.8 - Prob. 16PCh. 24.8 - Propose syntheses of the following compounds from...Ch. 24.8 - How would you prepare the following compounds from...Ch. 24.8 - Prob. 19PCh. 24.9 - Draw an orbital picture of thiazole. Assume that...Ch. 24.9 - Prob. 21PCh. 24.9 - Prob. 22PCh. 24.9 - Which nitrogen atom in the hallucinogenic indole...Ch. 24.9 - Prob. 24PCh. 24.10 - Prob. 25PCh. 24.SE - Name the following amines, and identify each as...Ch. 24.SE - The following compound contains three nitrogen...Ch. 24.SE - Name the following amine, including R, S...Ch. 24.SE - Prob. 29VCCh. 24.SE - Predict the product(s) for each reaction below and...Ch. 24.SE - Predict the product(s) and provide the complete...Ch. 24.SE - Prob. 32MPCh. 24.SE - Predict the product(s) and provide the mechanism...Ch. 24.SE - The diazotization of aniline first involves the...Ch. 24.SE - Prob. 35MPCh. 24.SE - Prob. 36MPCh. 24.SE - Prob. 37MPCh. 24.SE - Prob. 38MPCh. 24.SE - Choline, a component of the phospholipids in cell...Ch. 24.SE - Prob. 40MPCh. 24.SE - -Amino acids can be prepared by the Strecker...Ch. 24.SE - Prob. 42MPCh. 24.SE - Prob. 43MPCh. 24.SE - Prob. 44MPCh. 24.SE - Propose a mechanism for the following reaction:Ch. 24.SE - Prob. 46MPCh. 24.SE - Name the following compounds:Ch. 24.SE - Prob. 48APCh. 24.SE - Prob. 49APCh. 24.SE - Prob. 50APCh. 24.SE - Histamine, whose release in the body triggers...Ch. 24.SE - Prob. 52APCh. 24.SE - Prob. 53APCh. 24.SE - Prob. 54APCh. 24.SE - Prob. 55APCh. 24.SE - Prob. 56APCh. 24.SE - Prob. 57APCh. 24.SE - Prob. 58APCh. 24.SE - Prob. 59APCh. 24.SE - Prob. 60APCh. 24.SE - Show the products from reaction of p-bromoaniline...Ch. 24.SE - Prob. 62APCh. 24.SE - How would you prepare the following compounds from...Ch. 24.SE - Prob. 64APCh. 24.SE - Phenacetin, a substance formerly used in...Ch. 24.SE - Prob. 66APCh. 24.SE - Draw the structure of the amine that produced the...Ch. 24.SE - Fill in the missing reagents a-e in the following...Ch. 24.SE - Prob. 69APCh. 24.SE - Prob. 70APCh. 24.SE - Deduce the structure of the compound with formula...Ch. 24.SE - Prob. 72APCh. 24.SE - Prob. 73APCh. 24.SE - Prob. 74APCh. 24.SE - Prob. 75APCh. 24.SE - Prob. 76APCh. 24.SE - Propose a structure for the product with formula...Ch. 24.SE - Prob. 78APCh. 24.SE - Prob. 79APCh. 24.SE - Prob. 80APCh. 24.SE - Prob. 81APCh. 24.SE - Prob. 82APCh. 24.SE - Prob. 83APCh. 24.SE - Prob. 84AP
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- How could you use 1H NMR, 13C NMR, and IR spectroscopy to help you distinguish between the following structures?arrow_forwardwhat is the structure for this H NMR, C5H9BrO2 HDI = 1arrow_forwardWhich best describes a characteristic of the NMR spectra for amines? O secondary amine have N-H signals around бH 6.0 O protons on the a carbon are more deshielded than protons on the ẞ carbon O C13 signals for the a carbon of an aliphatic amine appear around ō 20 O protons on the ẞ carbon absorb around б 1.3arrow_forward
- According to this H NMR spectrum, identify the structure of the compound. the only additional information given is the molecular weight is 240.3 14 72 7.0 8 (ppm) 6.8 6.4 3.0 2.5 2.0 6 tppm)arrow_forwardAttached is the 1H NMR spec for phenylethylamine. Draw the structure of the amine on the spectrum, and identify each peak (e.g. a labeled H atom on your structure, TMS, etc.)arrow_forwardDraw the structure of a compound with the molecular formula C9H10O2 that produces the following 1H NMR spectrum and 13C NMR spectrum.arrow_forward
- Indicate the shift of carbon bonded to an alcohol (-CH₂-OH) (in ppm) in a ¹³C NMR spectrum. 20 90 60 135 O210arrow_forwardA compound has the molecular formula: C4H8O2 and gives the following C-13 NMR spectrum. Provide the most likely functional groups for each signal. nmrsim presentation 1 1 C:Bruken Topspin3.5pl7 examdata -170.7658 150 100 d 170.8 (O CH3) ; 60.4 (OCH2); 20.8, 14.1 (2 x C=0) 8170.8 (0 CH₂); 60.4 (OCH₂); 20.8, 14.1 (2 x CH3). 8 170.8 (CH3); 60.4 (C-0); 20.8, 14.1 (2 x OCH₂) 8170.8 (C=0); 60.4 (OCH₂); 20.8, 14.1 (2 x CH3). 8170.8 (C) ; 60.4 (O CH2); 20.8, 14.1 (2 x O CH3) -60.4293 50 -20.7902 -14.1385 [ppm] [+]arrow_forwardWhich one of the following compounds (from Figure #7) produced the 'H NMR spectrum (from Figure #8) shown below? Figure #7 inte compound A compound B compound C compound D Please click here if image does not display. Figure #8 3 203938 PPM 10 9 8 7 5 4 3 2 1 8 (ppm) Please click here if image does not display. O compound A O compound D O compound C O compound Barrow_forward
- The following NMR spectra were obtained from a compound with the molecular formula C4H6O. Use this information to predict its structure.arrow_forwardDraw the structure of the compound identified by the simulated 'H NMR and C NMR spectra. The molecular formula of the compound is C,0H,O. 12 (Blue numbers next to the lines in the 'H NMR spectra indicate the integration values.) H NMR 1H 2H 2H 2H 2H|| 3H 10 8. 4 (dd) g 13C NMR 220 200 180 160 140 120 100 80 60 40 20 8 (ppm) Deduce the structure from the spectra. Select Draw Rings More Erasearrow_forwardThe 1H-NMR spectrum of Compound C shows five signals – δ 2.38 (1H, dt), 2.72 (1H, dt), 5.34 (1H, t), 5.49 (2H, ddd), 6.27 (2H, dd) ppm. Its 13C-NMR spectrum has four signals – δ 26, 58, 127, 129 ppm. In the compound’s mass spectrum, the M+1 peak appears at m/z = 115. An M+2 peak, whose intensity is roughly one-third that of the M+1 peak, also appears. Suggest a structure for this compound.arrow_forward
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