Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter FRP, Problem 26P
Compound Y
Figure 1 The IR spectrum of compound Y (Problem 34)
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The 'H NMR and 13C spectra of a compound with a molecular formula of C6H12O2 are shown below.
1. Name the compound in the textbox below.
2. Draw a possible structure for this compound.
1Η NMR
2H 2H
2H
3HPPM
3H
13C NMR
220
200
100
140
100
120
PPM
Thymol (molecular formula C10H14O) is the major component of the oil of thyme. Thymol shows IR absorptions at 3500–3200, 3150–2850, 1621, and 1585 cm−1. The 1H NMR spectrum of thymol is given below. Propose a possible structure for thymol.
Propose a structure for D (molecular formula CgH,CIO,) consistent with the given spectroscopic data.
13C NMR signals at 30, 36, 128, 130, 133, 139, and 179 ppm
1Η ΝMR of D
4H
2H
2 H
1H
12
10
8
4
2
ppm
Chapter FRP Solutions
Organic Chemistry
Ch. FRP - Prob. 1PCh. FRP - 2. Which member of these pairs is the more polar?...Ch. FRP - 5. Though they each contain only one type of...Ch. FRP - Predict the products from each of the following...Ch. FRP - Prob. 5PCh. FRP - Prob. 6PCh. FRP - Prob. 7PCh. FRP - Prob. 8PCh. FRP - Predict the products from each of the following...Ch. FRP - Prob. 10P
Ch. FRP - 13. Starting with propyne and using any other...Ch. FRP - Bromination of 2-methylbutane yields predominantly...Ch. FRP - An alkane (A) with the formula C6H14 reacts with...Ch. FRP - Prob. 14PCh. FRP - Prob. 15PCh. FRP - Dehydrohalogenation of meso-1, 2-dibromo-1,...Ch. FRP - Prob. 17PCh. FRP - Prob. 18PCh. FRP - 27. (R)-3-Methyl-1-pentene is treated separately...Ch. FRP - Prob. 20PCh. FRP - Prob. 21PCh. FRP - Prob. 22PCh. FRP - Prob. 23PCh. FRP - Synthesize the following compound by a method that...Ch. FRP - Provide three methods that employ Grignard...Ch. FRP - 34. Compound Yexhibits one NMR signal at (a...Ch. FRP - Prob. 27PCh. FRP - 36. Compound X shows a strong IR absorption band...Ch. FRP - Prob. 29PCh. FRP - 38. In addition to more highly fluorinated...Ch. FRP - Fluorination of (R)-2-flurobutane yields a mixture...Ch. FRP - Prob. 32PCh. FRP - Prob. 33P
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- Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardA compound with molecular formula C8H8O3 exhibits the following IR, 1H NMR and 13C NMR spectra. Deduce the structure of this compound.arrow_forwardDetermine the structure of an alcohol with molecular formula C5H12O that exhibits the following signals in its 13C NMR spectra: a. Broadband decoupled: 73.8 δ, 29.1δ, and 9.5 δ b. DEPT-90: 73.8 δ c. DEPT-135: positive signals at 73.8 δ, and 9.5 δ, and negative signal at 29.1δ,arrow_forward
- 3. Propose a structure for an organic compound with molecular formula C3H1404 given the following 'H NMR and IR spectra. Draw the structure only, no need to interpret the spectra. 1H NMR Spectrum IR Spectrum Triplet Singlet d (6H) 8 (4H) 8 (4H) 1740 cm1 Quartetarrow_forwardDeduce the structure of a compound with molecular formula C5H100 that exhibits the following ¹H and ¹³C NMR spectra. IH NMR CNMR 150 10 Structure A Structure B Structure C Structure D 24 1C 100 B 2H H 20 50 10 D 311arrow_forwardQ2: The proton NMR spectrum is shown for a compound with formula C5H9NO4. The infrared spectrum displays strong bands at 1750 and 1562 cm-1 and a medium-intensity band at 1320 cm-1. The normal carbon- 13 and the DEPT experimental results are tabulated. Draw the structure of this compound. Normal Carbon DEPT-135 DEPT-90 14 ppm Positive No peak No peak 16 Positive 63 Negative No peak 83 Positive Positive 165 No peak No peak Proton spectrum C;H,NO4 0.92 2.01 3.00 3.00 5.0 4.5 4.0 3.5 3.0 25 2.0 1.5 10 0.5 0.0arrow_forward
- Given the following 13C NMR signals, construct a structure for the unknown compounds. A. Molecular formula: C6H14O DEPT-135 (positive): 14.1 δ DEPT-135 (negative): 22.7 δ, 25.3 δ, 31.8 δ, 32.2 δ, 62.8 δ B. Molecular formula: C7H12O2 Broadband decoupled: 19.1 δ, 28.0 δ, 70.5 δ, 129.0 δ, 129.8 δ, 165.8 δ DEPT-90: 28.0 δ, 129.8 δ DEPT-135 (positive): 19.1 δ, 28.0 δ, 129.8 δ DEPT-135 (negative): 70.5 δ, 129.0 δarrow_forwardQ3: The proton NMR spectrum of a compound with formula C5H100 is shown. The DEPT experimental results are tabulated. The infrared spectrum shows medium-sized bands at 2968, 2937, 2880, 2811, and 2711 cm1 and strong bands at 1728 cm-1. Draw the structure of this compound. Normal Carbon DEPT-135 DEPT-90 11.35 ppm No peak No peak No peak Positive 12.88 Positive 23.55 Negative 47.78 Positive Positive 205.28 Positive Positive (C=0) T m 240 2.35 2.30 2.25 2.20 0.75 0.91 1.04 1.01 2.90 2.92 9.6 9'5 24 23 2.2 2.1 2.0 1.9 1.8 1.7 1.6 14 1.3 1.2 1.1 10 0.9 2890.2 \ 2888.0 690.2 0'889 F189¬ 669.6 667.8arrow_forwardWhat is the structure of the compound if its formula is C5H10O, it exhibits 13C-NMR signals Broadband decoupled: 207, 45, 28, and 12 ppm DEPT-90: no signals DEPT-135: positive signals at 28 and 12 ppm; negative signals at 45 and 16 ppm.arrow_forward
- Propose a structure for compound X (molecular formula C6H12O2), which gives a strong peak in its IR spectrum at 1740 cm−1. The 1H NMR spectrum of X shows only two singlets, including one at 3.5 ppm. The 13C NMR spectrum is given below. Propose a structure for X.arrow_forwardAn unknown compound with molecular formula C9H180 forms a phenylhydrazone, but gives a negative with Tollens' test. The IR spectrum has a strong band near 1710 cm. The broadband proton- decoupled "C NMR spectrum is given below. Propose a structure for the unknown compound. Explain your answer based on the given spectroscopic data CH3 A, C3H180 CH2 CH CDCI3 TMS 220 200 180 160 140 120 100 80 60 40 20 S, (ppm)arrow_forwardDraw 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)arrow_forward
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