Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 12.SE, Problem 49AP
The infrared spectrum of the compound with the mass spectrum shown below has a medium-intensity peak at about 1650 cm-1. There is also a C-H out-of-plane bending peak near 880 cm-1. Propose a structure consistent with the data.
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Chapter 12 Solutions
Organic Chemistry
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- The infrared spectrum of the compound with the mass spectrum shown below lacks any significant absorption above 3000 cm-1. There is a prominent peak near 1740 cm-1 and another strong peak near 1200 cm-1. Propose a structure consistent with the data.arrow_forwardCompound E is a volatile organic liquid with a fruity smell. Its mass spectrum is given below. Identify the fragments at m/z 77 and 105, then propose a structure for this compound.arrow_forwardPART 2: Compounds A, B, and C are isomers with the formula C5H11Br. Their broadband proton-decoupled 13C NMR spectra are given below. Information from the DEPT 13C NMR spectra is given near each peak. Give structure for C.arrow_forward
- Compounds A, B, and C are isomers with the formula C5H11Br. Their broadband proton-decoupled 13C NMR spectra are given below. Information from the DEPT 13C NMR spectra is given near each peak. Give structures for A and B. (Note: part 2 will be posted).arrow_forwardA compound has strong infrared absorptions at the following frequencie . Suggest likely functional group that may be present. Q.) 1710 and 2500–3400 (broad) cm-1arrow_forwardComplete the following answer using the data provided here: Molecular formula: C4H8O2 Important IR data (cm-1): 3280 (broad); 2980-2730 (many); 1690; 1254 All 1H NMR data (ppm, splitting, integration): 11.0 ppm (s), 1; 2.57 ppm (m), 1; 1.07 ppm (d), 6 1. Sketch out a 1H NMR spectrum showing peak locations and peak splitting on a ppm scale for the data provided above. Include the data labels above in your spectrum, but do not show integration lines. 2. draw the most proper line bond structure for the data given abovearrow_forward
- Treatment of compound D with LiAlH4 followed by H2O forms compound E. D shows a molecular ion in its mass spectrum at m/z = 71 and IR absorptions at 3600–3200 and 2263 cm–1. E shows a molecular ion in its mass spectrum at m/z = 75 and IR absorptions at 3636 and 3600–3200 cm–1. Propose structures for D and E from these data and the given 1H NMR spectra.arrow_forwardcompound with the molecular formula C7H9N exhibits IR bands at 3450 cm-1 (medium, doublet), and 855 cm-1 (strong) and shows the following major mass spectral signals (m/z): 106 (base); 107 (M+, about 70% of base), 91 (40% of base), and 77 (about 20% of base). Deduce a reasonable structure from this data.arrow_forwardCompound C shows a molecular ion at m/z 148 and other prominent peaks at m/z 105 and 77. Following are its infrared and 1H-NMR spectra. Q.) Account for the appearance of peaks in its mass spectrum at m/z 105 and 77.arrow_forward
- Propose structures that are consistent with the following spectra. (Integral ratios are given from left to right across the spectrum.) a. The 1H NMR spectrum of a compound with molecular formula C4H10O2 has two singlets with integral ratios of 2 : 3. b. The 1H NMR spectrum of a compound with molecular formula C6H10O2 has two singlets with integral ratios of 2 : 3. c. The 1H NMR spectrum of a compound with molecular formula C8H6O2 has two singlets with integral ratios of 1 : 2.arrow_forwardThe tabulated 1H NMR and 13C NMR spectral data acquired for an unknown compound with an atomic composition of C11H20O2is detailed below. Using this data, propose a molecular structure for the unknown compound and, based on this structure, hypothesise a molecular structure of at least one major fragment appearing in the corresponding EI mass spectrum of the unknown compound, which is shown below; 1H NMR (500 MHz, Chloroform-d) δ 5.55 (s, 1H), 5.11 (d, J = 5.8 Hz, 1H), 4.16 (q, J = 6.3 Hz, 2H), 2.22 (d, J = 6.1 Hz, 2H), 2.18 (d, J = 6.1 Hz, 2H), 2.13 (s, 3H), 1.65 (s, 3H), 1.61 (s, 3H), 1.27 (t, J = 6.3 Hz, 3H). 13C NMR (125 MHz, Common NMR Solvents) δ 166.72 (C), 158.99 (C), 131.99 (C), 123.58 (CH), 116.45 (CH), 59.71 (CH2), 38.94 (CH2), 26.53 (CH2), 24.98 (CH3), 19.87 (CH3), 18.90 (CH3), 14.53 (CH3).arrow_forwardPropose a structure consistent with each set of data. C10H14: IR absorptions at 3150–2850, 1600, and 1500 cm−1arrow_forward
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