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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_forwardTreatment of ketone A with ethynyllithium (HC≡CLi) followed by D3O+ afforded a compound B of molecular formula C12H13DO3, which gave an IR absorption at approximately 1715 cm−1. What is the structure of B and how is it formed?arrow_forward
- When 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_forwardTreatment 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_forwardAn unknown compound C3H2NCl shows moderately strong IR absorptions around 1650 cm-1 and 2200 cm-1. Its NMR spectrum consists of two doublets (J = 14 Hz) at δ 5.9 and δ 7.1. Propose a structure consistent with this data?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_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_forwardOn the basis of the molecular formula, 1H NMR data, and IR data provided, propose a consistent structure. Moleculal Formula: C2H3Cl31H NMR data: δ 3.95 (d, 2H), 5.77 (t, 1H)IR data: 2950 cm–1, and several peaks below 820 cm–1.arrow_forward
- Reaction 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_forwardCompounds 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_forwardA compound of formula C5H11Br has the following 1H NMR characteristics: Singlet,6H; Triplet,3H; Quartet,2H. Provide a structure for the compound consistent with this information. Support your answer.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning