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Chapter 17 Solutions
ORGANIC CHEMISTRY-ETEXT REG ACCESS
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- 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?arrow_forwardAddition of m-xylene to the strongly acidic solvent HF/SbF5 at 45C gives a new species, which shows 1H-NMR resonances at 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.arrow_forwardWhen compound X (C15H17N) is treated with bezenesulfonyl chloride and aqueous potassium hydroxide, no apparent change occurs. Acidification of the mixture gives a clear solution. Propose a structure for X based on the given 1H NMR spectra. Explain your answer by interpreting the spectraarrow_forward
- Treatment of benzoic acid (C6H5CO2H) with NaOH followed by 1-iodo-3methylbutane forms H. H has a molecular ion at 192 and IR absorptions at 3064, 3035, 2960−2872, and 1721 cm−1. Propose a structure for H.arrow_forwardA hydrocarbon, compound B, has molecular formula C6H6, and gave an NMR spectrum with two signals: delta 6.55 pm and delta 3.84 pm with peak ratio of 2:1. When warmed in pyridine for three hr, compound B quantitatively converts to benzene. Mild hydrogenation of B yielded another compound C with mass spectrum of m/z 82. Infrared spectrum showed no double bonds; NMR spectrum showed one broad peak at delta 2.34 ppm. With this information, address the following questions. a) How many rings are in compound C? b) How many rings are probably in B? How many double bonds are in B? c) Can you suggest a structure for compounds B and C? d) In the NMR spectrum of B, the up-field signal was a quintet, and the down field signal was a triplet. How must you account for these splitting patterns?arrow_forwardThe 1H-NMR spectrum of Compound D of molecular formula C10H12O shows three singlets – δ 2.20 (6H, s), 4.86 (4H), 7.10 (2H) ppm. Its 13C-NMR spectrum has five signals – 20, 74, 127, 135, 146 ppm. Suggest a structure for this compound.arrow_forward
- Compounds W and X are isomers. They have the molecular formula C9H8O. The IR spectrum ofeach compound shows a strong absorption band near 1715 cm−1. Oxidation of either compound withhot, basic potassium permanganate followed by acidification yields phthalic acid. The proton NMRspectrum of W shows a multiplet at δ 7.3 and a singlet at δ 3.4. The proton NMR spectrum of Xshows a multiplet at δ 7.5, a triplet at δ 3.1, and a triplet at δ 2.5. Propose structures for W and X.arrow_forwardTreatment 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_forwardReaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed bytreatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is thestructure of R?arrow_forward
- Compounds A and B are isomers having the molecular formula C4H8O3. Identify A and B on the basis of their 1H NMR spectra.Compound A: δ 1.3 (3H, triplet); 3.6 (2H, quartet); 4.1 (2H, singlet); 11.1 (1H, broad singlet)Compound B: δ 2.6 (2H, triplet); 3.4 (3H, singlet); 3.7 (2H triplet); 11.3 (1H, broad singlet)arrow_forwardReaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed by treatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 18.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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