Treatment of compound D with LIAIH, followed by H,O 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. E shows a molecular ion in its mass spectrum at m/z= 75 and IR absorptions at 3636 and 3600 – 3200 cm1. Propose structures for D and E from these data and the given 'H NMR spectra. Part 1 out of 2 1H NMR of D 2 H 2 H 1 H 8 7 4 3 1 ppm -LO CO

Treatment of compound D with LIAIH, followed by H,O 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. E shows a molecular ion in its mass spectrum at m/z= 75 and IR absorptions at 3636 and 3600 – 3200 cm1. Propose structures for D and E from these data and the given 'H NMR spectra. Part 1 out of 2 1H NMR of D 2 H 2 H 1 H 8 7 4 3 1 ppm -LO CO

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy

Section12.SE: Something Extra

Problem 50AP

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Benzonitrile (C6H5CN) is reduced to two different products depending on the reducing agent used. Treatment with lithium aluminum hydride followed by water forms K, which has a molecular ion in its mass spectrum at 107 and the following IR absorptions: 3373, 3290, 3062, 2920, and 1600 cm-1. Treatment with a milder reducing agent forms L, which has amolecular ion in its mass spectrum at 106 and the following IR absorptions: 3086, 2820, 2736, 1703, and 1600 cm-1. L shows fragments in its mass spectrum at m/z = 105 and 77. Propose structures for K and L and explain how you arrived at your conclusions.
Compound 1, was found to consist of C,H,N, and Cl with an elemental analysis of 61.1% C, 2.9% H, and 10.2% N. IR Spectra displayed absorbances at 2215, 1605. Deduce the structure of this compound. (there is only one Cl)
(a) Compound A has molecular formula C9H18O but shows only one singlet in the 1H-NMR spectrum. Suggest a structure for A and explain your reasoning. (b) Compound B has molecular formula C10H14. The IR, mass, 1H-NMR, and 13C-NMR speca are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for B and explain your reasoning.
The NMR spectra for compound 1 were acquired in a 7.5 mg / 0.6 mL solution ofCDCl3 The 1H and 13C peaks are also listedbelow. Provide a analysis of the NMR spectra for compound 1 include rationalisation of COSY1H NMR (400 MHz, CDCl3) δ 7.73 (d, J = 9.5 Hz, 1H), 7.56 (ddd, J = 8.5, 7.5, 1.6 Hz, 1H),7.51 (dd, J = 7.5, 1.6 Hz, 1H), 7.36 (d, J = 8.5 Hz, 1H), 7.30 (dd, J = 8.5, 7.5 Hz, 1H), 6.45(d, J = 9.5 Hz, 1H).13C NMR (101 MHz, CDCl3) δ 160.79, 154.09, 143.43, 131.85, 127.87, 124.44, 118.86,116.94, 116.74.
Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added NaOCOCH3 forms compound A. A has amolecular ion in its mass spectrum at 154 and a strong peak in its IRspectrum at 1730 cm−1, in addition to C—H stretching absorptions.Without added NaOCOCH3, oxidation of citronellol with PCC yieldsisopulegone, which is then converted to B with aqueous base. B has amolecular ion at 152 and a peak in its IR spectrum at 1680 cm−1, inaddition to C—H stretching absorptions. a.) Identify the structures of A and B.b.) Draw a mechanism for the conversion of citronellol to isopulegone.c.) Draw a mechanism for the conversion of isopulegone to B.
Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added NaOCOCH3 forms compound A. A has a molecular ion in its mass spectrum at 154 and a strong peak in its IR spectrum at 1730 cm−1, in addition to C—H stretching absorptions. Without added NaOCOCH3, oxidation of citronellol with PCC yields isopulegone, which is then converted to B with aqueous base. B has a molecular ion at 152 and a peak in its IR spectrum at 1680 cm−1, in addition to C—H stretching absorptions.a.Identify the structures of A and B. b.Draw a mechanism for the conversion of citronellol to isopulegone. c.Draw a mechanism for the conversion of isopulegone to B.
C9H10O2: IR absorption at 1718 cm–1. Propose a structure with data given.
compound 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.
Treatment of compound E (molecular formula C4H8O2) with excessCH3CH2MgBr yields compound F (molecular formula C6H14O) afterprotonation with H2O. E shows a strong absorption in its IR spectrum at1743 cm−1. F shows a strong IR absorption at 3600−3200 cm−1. The 1HNMR spectral data of E and F are given. What are the structures of E andF?Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppm Compound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4H), and 1.55 (singlet, 1 H) ppm
Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.
3-Chlorocyclopropene, on treatment with AgBF4, gives a precipitate of AgCl and a stable solution of a product that shows a single 1H NMR absorption at 11.04 Î´. What is a likely structure for the products, and what is its relation to HĂ¼ckelâ€™s rule?
Reaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G? We will learn about the details of this reaction in Chapter 22.