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How many peaks would you expect to see in the 13C NMR spectrum of 3-bromohexane?
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- 4. a. The ¹H NMR spectrum of a compound with the molecular formula C3H₁0O₂ is shown below (integral values are given above each set of peaks). Analysis of its ¹3C NMR spectrum shows peaks at 174, 61, 27, 14 and 9 ppm (see the posted lecture notes for June 7 for some guidance on ¹³C NMR spectroscopy). The IR spectrum shows a prominent peak at 1735 cm¹¹ and no peaks with a stretching frequency above 3000 cm³¹. What is the structure of this compound? 3.0 b. Which peak in the NMR spectrum in part a corresponds to a CH₂ group (called a "methylene") bonded to an O atom? a. 1.12 ppm b. 1.25 ppm c. 2.31 ppm e. There are no CH₂ groups bonded to an O atom in this compound. d. 4.12 ppm 1.0 PPMCamphor, a saturated monoketone from the Asian camphor tree, is used among other things as a moth repellent and as a constituent of embalming fluid. If camphor has M+=152.1201 by high-resolution mass spectrometry, what is its molecular formula? How many rings does camphor have?Analyze the high resolution proton NMR spectrum of a compound with the molecular formula C8H16O2 and find out which one. A. 2-ethylhexanoic acid B. 1,4-cyclohexanedimethanol C. ethyl hexanoate D. butyl butyrate E. ethyl 2,2-dimethylpropanoate
- į. A sample of edible oil was subjected to analysis using mass spectrometry (MS). The following mass spectra (X and Y) were obtained. The spectra represent 2,4- decadienal and squalene. Identify the spectrum of 2,4-decadienal and squalene and explain your answer. H3C. H 2,4-decadienal Squalene 81 0.2- 0.1 -41 67 95 1231 L 10352 100 200 300 400 500 m/z X 0.2- 69 0.15 - 81 0.1 - 0.05 .41 95 10949,7520sg83P8732 334136BDE234494891 100 200 300 400 500 m/z Y Scaled Intensity Scaled Intensity6. IR spectroscopy experiment is used to evaluate the success of the reaction. The IR spectra for acetaminophen and phenacetin are shown below. a. Identify which spectrum is for acetaminophen and which is for phenacetin. b. Label the key bond/functional group signals on each spectrum. (eg N-H, C=0, O-H, C=C, C(sp2)-H, C(sp3)-H) OH N H acetaminophen phenacetin 100.0 90 80 70 60 30 40 30 20 10 0.0 40000 3000 2000 1500 1000 400.0 em-1 LOD D 4D00 3000 s0o 2000 1500 10006. 'H-NMR data for three isomers of C5H1,Br, is given below. Give the structure of each isomer. a. 8 1.0 , s, 9H 8 5.3, s, 1H b. 8 1.0, t, 6H 8 2.4, q, 4H c. 8 1.3, m, 2H 8 1.85, m, 4H 8 3.35, t, 4H
- 7. Identify the structures for the following two isomers with molecular formula C10H12O2. There is an IR stretch at 1718 cm¹ for the compound in part a and 1740 cm¹ for the compound in part b. The 'H NMR spectra are shown below. a. b. 11 10 HSP-01-396 11 10 HSP-02-824 3 2 2 will 9 9 2 8 8 5 7 7 6 6 5 ppm 5 ppm 4 3 2 2 4 3 2 2 3 1 1 0 0What is the standard solvent in both 1H and 13C NMR? A. (CH3)4Si B. D2O C. CDCl3 D. C6H6 E. none of the aboveQ4. The following is the 13C NMR spectrum of a highly concentrated solution of dicyclopentadiene obtained in chloroform-d. Despite the high purity of the compound based on ¹H NMR, there is a massive peak observed at 77.2 ppm in this 13C spectrum, which doesn't correspond to any resonances expected for dicyclopentadiene. What is this peak, and why do you not see a corresponding peak for this compound in your ¹H NMR spectrum? 79-751 <-136.22 -132.62 132.27 132.23 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30
- Dr. N. M. Arr was called in to help analyze the 1H NMR spectrum of a mixture of compounds known to contain only C, H, and Br. The mixture showed two singlets—one at 1.8 ppm and the other at 2.7 ppm—with relative integrals of 1 : 6, respectively. Dr. Arr determined that the spectrum was that of a mixture of bromomethane and 2-bromo-2-methylpropane. What was the ratio of bromomethane to 2-bromo-2-methylpropane in the mixture?1. An aliphatic ketone absorbs at 1,715 cm-1. What is the frequency of this vibration in hertz, which is cycles per second or just per second, reciprocal seconds? 2. What is the energy equivalent of this stretching vibration in kcal/mole? 3. Why does 3,4-diethyl-3-hexene not have a carbon to carbon double bond stretching absorption band? 4. Why does a carbon to oxygen double bond absorption band have a greater intensity than a carbon to carbon double bond absorption band? 5. Using only IR, explain in detail how one could most easily differentiate between oct-1-ene and oct-1-yne if all carbon to carbon bonds are ignored. 6. Using only IR, explain in detail how one could most easily differentiate between butan-1-ol and butanoic acid.A and B, isomers of molecular formula C3H5Cl3, are formed by the radical chlorination of a dihalide C of molecular formula C3H6Cl2. a.Identify the structures of A and B from the following 1H NMR data: Compound A: singlet at 2.23 and singlet at 4.04 ppm Compound B: doublet at 1.69, multiplet at 4.34, and doublet at 5.85 ppm b.What is the structure of C?