Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter FRP, Problem 28P
Compound X
Figure 2 The broadband proton-decoupled
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C5H10O2 H
Determine H and C Spectra for the compund
13
The proton NMR spectrum for a compound with formula C10H12O2is shown below.The infrared spectrum has a strong band al 1711 cm-1. The normal carbon-13 NMRspectral results are tabulated along with the DEPT-135 and DEPT-90 information. Drawthe structure of this compound.
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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- The 1H and 13C NMR spectra of compound A, C8H9Br, are shown. Propose a structure for A, and assign peaks in the spectra to your structure.arrow_forwardCompound A, a hydrocarbon with M+=96 in its mass spectrum, has the 13C spectral data given below. On reaction with BH3, followed by treatment with basic H2O2. A is converted into B, whose, 13C spectral data are also given below. Propose structures for A and B. Compound A Broadband-decoupled l3C NMR: 26.8, 28.7, 35.7, 106.9, 149.7 DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 Compound B Broadband-decoupled 13C NMR: 26.1, 26.9, 29.9, 40.5, 68.2 DEPT-90: 40.5 DEPT-135: positive peak at 40.5 ; negative peaks at 26.1, 26.9. 29.9, 68.2arrow_forwardMass spectrometry of an unknown compound revealed a molecular ion at m/z 100.09. The IR spectrum, the ¹³C NMR spectrum, and the ¹H NMR spectrum are shown below. Draw the structure of this compound. 4000 220 3000 200 180 160 2000 M 1500 Wavenumbers (cm-¹) 140 120 100 1H 80 6H 1000 40 3H 20 ppm 500arrow_forward
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- Q4: The proton NMR spectrum of a compound with formula C8H14O2 is shown. The DEPT experimental results are tabulated. The infrared spectrum shows medium-sized bands at 3055, 2960, 2875, and 1660 cm-1 and strong bands at 1725 and 1185 cm-1. Draw the structure of this compound. Normal Carbon DEPT-135 DEPT-90 10.53 ppm Positive No peak Positive No peak No peak No peak 12.03 14.30 Positive 22.14 Negative No peak No peak 65.98 Negative 128.83 No peak 136.73 Positive Positive 168.16 No peak No peak (C=0) 0.97 2.05 7.92 2.96 7.0 6.5 60 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0arrow_forward11 10 9 8 7 9 +6 5 -3 2 1 ppmarrow_forwardCompound CsH12 gives the following H-NMR. Draw the structure of the compound. Draw a box around the structure you want graded. 5.00 1.00 6.04 70 6.5 6.0 4.0 3.5 3.0 25 20 1.5 A student was adding bromine across the double bond of 2-butene to make 2,3-dibromobutane. After taking the NMR, the student discovered they didn't get the product expected. Based on the NMR, what product did they obtain? Draw a box around your answer. 1.00 2.01 |2.00 3.00arrow_forward
- An unknown compound D exhibits a strong absorption in its IR spectrumat 1692 cm−1. The mass spectrum of D shows a molecular ion at m/z =150 and a base peak at 121. The 1H NMR spectrum of D is shown below.What is the structure of D?arrow_forwardGive and explain the analysis of H-NMR and C-NMR spectra of the followingarrow_forwardDraw the structure of molecular formula C8H10O that produced the 1H NMR spectra shown below. The IR spectrum does not show a broad absorbance at 3300 cm–1 or a strong absorbance at 1710 cm–1.arrow_forward
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