Reaction of pentanoyl chloride (CH3CH2CH2CH2COCl) with lithium dimethyl cuprate [LiCu(CH3)2] forms a compound J that has a molecular ion in its mass spectrum at 100, as well as fragments at m/z = 85, 57, and 43 (base). The IR spectrum of J has strong peaks at 2962 and 1718 cm-1. Propose a structure for J.

Reaction of pentanoyl chloride (CH3CH2CH2CH2COCl) with lithium dimethyl cuprate [LiCu(CH3)2] forms a compound J that has a molecular ion in its mass spectrum at 100, as well as fragments at m/z = 85, 57, and 43 (base). The IR spectrum of J has strong peaks at 2962 and 1718 cm-1. Propose a structure for J.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter22: Reactions Of Benzene And Its Derivatives

Section: Chapter Questions

Problem 22.10P: Addition of m-xylene to the strongly acidic solvent HF/SbF5 at 45C gives a new species, which shows...

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Treatment of benzaldehyde (C6H5CHO) with Zn(Hg) in aqueous HCl forms a compound Z that has a molecular ion at 92 in its mass spectrum. Z shows absorptions at 3150–2950, 1605, and 1496 cm-1 in its IR spectrum. Give a possible structure for Z.
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.
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.
Reaction of 2-methylpropanoic acid [(CH3)2CHCO2H] with SOCl2 followed by 2-methylpropan-1-ol forms X. X has a molecular ion at 144 and IR absorptions at 2965, 2940, and 1739 cm-1. Propose a structure for X.
Reaction of tert-butyl pentyl ether [CH3CH2CH2CH2CH2OC(CH3)3] with HBr forms 1-bromopentane (CH3CH2CH2CH2CH2Br) and compound B. B has a molecular ion in its mass spectrum at 56 and gives peaks in its IR spectrum at 3150−3000, 3000−2850, and 1650 cm−1. Propose a structure for B, and draw a stepwise mechanism that accounts for its formation.
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.
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?
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.
Ethers are not easily differentiated by their infrared spectra, but they tend to form predictable fragments in the mass spectrum. The following compounds give similar butdistinctive mass spectra.O Obutyl propyl ether butyl isopropyl etherBoth compounds give prominent peaks at m>z 116, 73, 57, and 43. But one compoundgives a distinctive strong peak at 87, and the other compound gives a strong peak at 101.Determine which compound gives the peak at 87 and which one gives the peak at 101.Propose fragmentations to account for the ions at m>z 116, 101, 87, and 73.
The tabulated 1H NMR and 13C NMR spectral data acquired for an unknown compound with an atomic composition of C11H20O2is detailed below. Using this data, propose a molecular structure for the unknown compound and, based on this structure, hypothesise a molecular structure of at least one major fragment appearing in the corresponding EI mass spectrum of the unknown compound, which is shown below; 1H NMR (500 MHz, Chloroform-d) δ 5.55 (s, 1H), 5.11 (d, J = 5.8 Hz, 1H), 4.16 (q, J = 6.3 Hz, 2H), 2.22 (d, J = 6.1 Hz, 2H), 2.18 (d, J = 6.1 Hz, 2H), 2.13 (s, 3H), 1.65 (s, 3H), 1.61 (s, 3H), 1.27 (t, J = 6.3 Hz, 3H). 13C NMR (125 MHz, Common NMR Solvents) δ 166.72 (C), 158.99 (C), 131.99 (C), 123.58 (CH), 116.45 (CH), 59.71 (CH2), 38.94 (CH2), 26.53 (CH2), 24.98 (CH3), 19.87 (CH3), 18.90 (CH3), 14.53 (CH3).
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.
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.