6. In the mass spectrum of 3-hexanone, alpha cleavage (cleavage of one of the C-C bonds of the carbonyl group) produces two peaks with what m/z values? A) 57 and 43 B) 71 and 29 C) 71 and 43 D) 57 and 71 E) 57 and 29 3-hexanone
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- 2. (9 points total) Each of the following Grignard reagents undergo reaction with CO₂ (solid). Grignard reagents: Number of ¹H NMR signals in the reaction product: CI A MgBr MeO B MgBr OMe MgBr Me MgCl a. (8 points) How many ¹H NMR signals do you expect to see in the spectrum of each product? Assume that the products are pure and that the carboxylic acid peak is present. Please write directly in the boxes. b. (1 point) Which Grignard reagent (A, B, C, or D) will lead to the product with the fewest ¹3C NMR signals?Ketones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+=74 in the mass spectrum?Propose structures for compounds that fit the following mass-spectral data: (a) A hydrocarbon with M+=132 (b) A hydrocarbon with M+=166 (c) A hydrocarbon with M+=84
- One way to determine the number of acidic hydrogens in a molecule is to treat the compound with NaOD in D2O, isolate the product, and determine its molecular weight by mass spectrometry. For example, if cyclohexanone is treated with NaOD in D2O, the product has MW = 102. Explain how this method works.Carvone is an unsaturated ketone responsible for the odor of spearmint. If carvone has M+=150 in its mass spectrum and contains three double bonds and one ring, what is its molecular formula?Camphor, 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?
- Mass spectrometry: The following alcohol can undergo alpha-cleavage. What is the m/z value of the peak resulting from the most favorable alpha-cleavage? OH alpha-cleavage O 84 O 58 O 59 O 73 O 74 171 & 24 4. 23 96 13 15 6. 43 EGO R F G C M4 23QUESTION 3 Predict the IR absorption bands (peaks) observed in the spectrum of 3-methylcyclohexanone. sp3 C-H stretching (-2850-2960 cm 1) sp2 C-H stretching (-3000-3100 cm-1) Alcohol O-H stretch (-3300 cm-1, broad) C-O double bond stretch (-1700 cm-1) Aromatic out of plane bend for monosubstitution (690-710 and 730-770 cm-1). Aromatic out of plane bend for para (1,4) disubstitution (810-840 cm-1). Aromatic out of plane bend for meta (1,3) disubstitution (690-750 and 750-810 cm 1). Aldehyde C-H stretch (2750 and 2850 cm-1). Carboxylic acid (carboxy group) O-H stretch (-2500-3000 cm-1, broad) N-H stretch (2 bands at -3400 cm-1) N-H bend (-1600 cm*1) Aromatic C-C double bond stretches (-1500 and 1600 cm-1). Aromatic overtones (1667-2000 cm-1) O O O OIn mass spectrometry, McLafferty Rearrangements are common in carbonyl compounds. Draw the daughter ion that would be observed in the mass spectrum resulting from McLafferty Rearrangement of this molecule. Drawing :O: Q
- 6. 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 1000(b) The 1H-NMR spectrum of compound B, C5 H10 O2, consists of the following signals: 8 1.2 (d, 6H), 2.0 (s, 3H), and 5 (septet, 1H); contains an ester. Draw the structural formula of compound B. • You do not have to consider stereochemistry. • Explicitly draw all H atoms. ୫) C n ? ChemDoodle ® Show HintFCompound 10 is a low-boiling liquid (boiling point 58 "C), that reacts with Br, in CCI, to form a 1,1,2,2-tetra bromide The Mass, RÄCÍTICAL SPECTROSCOPY FCompound 10 is a low-boiling liquid (boiling point 58 "C) that reacts with Br. in CCI, to form a 1,1,2,2-tetra bromiide The R, and 'H NMR spectra, along with "C NMR data ve aiven below Flemental Analysis:C. 48 36. H. 4.06; contains halogen. Mass Spectrum 39 74 50 60 140 150 160 170 180 190 200 30 40 70 80 90 100 110 120 130 mve Infrared Spectrum Wave Number, cm 1 4000 1000 2500 2000 1500 1300 1200 15D0 0 10c0 900 B00 700 15 12 13 14 15 Wavelength, microns " Η NMR ppm. 5 Structurei "C Spectral Data: doublet, 80.4 ppm singlet, 68.3 ppm triplet, 347 ppin 50.0m ude 02000 Brooks/Cole Publishing Company Absorbance