Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 13, Problem 13.22P
Propose structures consistent with each set of data: (a) a hydrocarbon with a molecular ion at
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Propose structures consistent with each set of data: (a) a hydrocarbon with a molecular ion at m/z = 68 and IR absorptions at 3310, 3000–2850, and 2120 cm-1; (b) a compound containing C, H, and O with a molecular ion at m/z = 60 and IR absorptions at 3600–3200 and 3000–2850 cm-1.
Treatment of anisole (CH3OC6H5) with Cl2 and FeCl3 forms P, which has peaks in its mass spectrum at m/z = 142 (M), 144 (M + 2), 129, and 127. P has absorptions in its IR spectrum at 3096–2837 (several peaks), 1582, and 1494 cm-1. Propose possible structures for P.
Mass spectra of butylcyclopentane and tert-butylcyclopentane were acquired. Spectrum A exhibited significant mass peaks at m/z values of 126, 97, 83, 69, 55, and 41. Spectrum B exhibited significant peaks at m/z values of 111, 69,57, and 41. Match each spectrum with its compound.
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - What is the mass of the molecular ion formed from...Ch. 13 - Prob. 13.2PCh. 13 - Use the following information to propose a...Ch. 13 - Prob. 13.4PCh. 13 - What molecular ions would you expect for the...Ch. 13 - The mass spectrum of 2,3-dimethylpentane also...Ch. 13 - The base peak in the mass spectrum of 2, 2,...Ch. 13 - (a) What mass spectral fragments are formed by ...Ch. 13 - What cations are formed in the mass spectrometer...Ch. 13 - The low-resolution mass spectrum of an unknown...
Ch. 13 - Benzene, toluene, and p-xylene BTX are often added...Ch. 13 - Prob. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - Prob. 13.15PCh. 13 - How do the IR spectra of the isomers cyclopentane...Ch. 13 - Problem 13.17 How do the three isomers of...Ch. 13 - Problem 13.18 What functional groups are...Ch. 13 - Problem-13.19 What are the major IR absorptions in...Ch. 13 - Problem-13.20 What are the major IR absorptions in...Ch. 13 - Problem-13.21 Which of the following possible...Ch. 13 - Problem-13.22 Propose structures consistent with...Ch. 13 - 13.23 What major IR absorptions are present above ...Ch. 13 - Problem-13.24 The mass spectrum of the following...Ch. 13 - Prob. 13.25PCh. 13 - Which compound gives a molecular ion at m/z= 122,...Ch. 13 - Propose two molecular formulas for each molecular...Ch. 13 - Propose four possible structures for a hydrocarbon...Ch. 13 - Problem-13.29 What is the molecular formula for...Ch. 13 - Problem-13.30 Propose a molecular formula for rose...Ch. 13 - 13.31 Match each structure to its mass spectrum
Ch. 13 - 13.32 Propose two possible structures for a...Ch. 13 - 13.33 What cations are formed in the mass...Ch. 13 - 13.34 and have the same molecular ion in the...Ch. 13 - 13.35 For each compound, assign likely...Ch. 13 - Prob. 13.36PCh. 13 - 13.37 Propose a structure consistent with each...Ch. 13 - 13.38 A low-resolution mass spectrum of the...Ch. 13 - 13.39 Primary alcohols often show a peak in their...Ch. 13 - 13.40 Like alcohols, ethers undergo α cleavage by...Ch. 13 - 13.41 Which of the highlighted bonds absorbs at...Ch. 13 - 13.42 What major IR absorptions are present above ...Ch. 13 - 13.43 How would each of the following pairs of...Ch. 13 - 13.44 Morphine, heroin, and oxycodone are three...Ch. 13 - 13.45 Reduction of cyclohex-2-enone can yield...Ch. 13 - Prob. 13.46PCh. 13 - 13.47 Match each compound to its IR spectrum
Ch. 13 - 13.48 Propose possible structures consistent with...Ch. 13 - A chiral hydrocarbon X exhibits a molecular ion at...Ch. 13 - 13.50 A chiral compound has a strong absorption...Ch. 13 - 13.51 Treatment of benzoic acid with followed by...Ch. 13 - 13.52 Treatment of benzaldehyde with in aqueous ...Ch. 13 - Prob. 13.53PCh. 13 - 13.54 Reaction of 2-methylpropanoic acid with ...Ch. 13 - 13.55 Reaction of pentanoyl chloride with lithium...Ch. 13 - Prob. 13.56PCh. 13 - 13.57 Treatment of anisole with and forms P,...Ch. 13 - 13.58 Reaction of with forms compound ,...Ch. 13 - Problem-13.59 The carbonyl absorption of an amide...Ch. 13 - Prob. 13.60PCh. 13 - Problem-13.61 Explain why a ketone carbonyl...Ch. 13 - 13.62 Oxidation of citronellol, a constituent of...
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- 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_forwardThe 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.arrow_forwardTreatment of 2-methylpropanenitrile [(CH3)2CHCN] withCH3CH2CH2MgBr, followed by aqueous acid, affords compound V, whichhas molecular formula C7H14O. V has a strong absorption in its IRspectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91(triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and2.60 (septet, 1 H) ppm. What is the structure of V?arrow_forward
- Treatment of compound D with LIAIH4 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 'H NMR spectra. 'H NMR of D 2H 2H 1H 8 7 6 2 ppmarrow_forwardIndicate two basic differences that exist between the spectra of 1H y 13C in NMR.arrow_forwardTreatment of alcohol A (molecular formula C5H12O) with CrO3, H2SO4, and H2O affords B with molecular formula C5H10O, which gives an IR absorption at 1718 cm−1. The 1H NMR spectrum of B contains the following signals: 1.10 (doublet, 6 H), 2.14 (singlet, 3 H), and 2.58 (septet, 1 H) ppm. What are the structures of A and B?arrow_forward
- (b) Determine the structure of an organic compound with a molecular ion at m/z 73 and absorption in its IR at 3300 (doublet) and 1680 cmarrow_forwardHow could 1H NMR spectroscopy be used to distinguish among isomers A, B, and C?arrow_forwardThe H1H1 NMR spectrum shown corresponds to an unknown compound with the molecular formula C6H10C6H10. There are no strong IR bands between 2100 and 2300 or 3250 and 3350 cm−1. Deduce and draw the structure of the molecule that corresponds to the spectrum.arrow_forward
- Draw the structure of a compound, CaH8O3 that exhibits IR absorptions at 1710 and 2500-3000 cm³¹ and the following ¹H NMR signals: 11.1 (1H, singlet), 4.14 (2H, singlet), 3.63 (2H, quartet), 1.26 (3H, triplet) ppm.arrow_forwardFollowing is the 1H-NMR spectrum of compound O, molecular formula C7H12. Compound O reacts with bromine in carbon tetrachloride to give a compound with the molecular formula C7H12Br2. The 13C-NMR spectrum of compound O shows signals at d 150.12, 106.43, 35.44, 28.36, and 26.36. Deduce the structural formula of compound O.arrow_forwardThe 'H NMR spectrum of 1,2-dimethoxyethane (CH;OCH,CH2OCH3) recorded on a 300 MHz NMR spectrometer consists of signals at 1017 Hz and 1065 Hz downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) At what frequency would each absorption occur if the spectrum were recorded on a 500 MHz NMR spectrometer?arrow_forward
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