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Treatment of benzaldehyde
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- Addition 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_forwardCompound 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.arrow_forwardNitriles, R–=C≡N, undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH3CH2C≡N, if it has IR absorptions from 2500–3100 cm-1 and at 1710 cm-1, and has M+=74?arrow_forward
- 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 δ. What is a likely structure for the products, and what is its relation to HĂ¼ckel’s rule?arrow_forwardAn aromatic compound K, whose molecular formula is C8H11N, is examined in the laboratory to elucidate its structure. The following observations were made: A) Compound K is soluble in dilute hydrochloric acid but insoluble in sodium hydroxide solution. B) Treatment of compound K with excess potassium hydroxide and benzenesulfonyl chloride, C(6)H(5)SO(2)Cl, results in the formation of a heterogeneous mixture. The NMR spectrum of compound K is shown below. C) Compound K when treated with acetic anhydride[CH3-C(O)-O-C(O)-CH3], gives compound L, whose molecular formula is C(10)H(13)ON. Compound L is insoluble in dilute acid or dilute base at room temperature, heating compound L in dilute acid or base, however, regenerates compound K. D) When compound L is heated with a mixture of concentrated nitric acid and sulfuric acid, a single product, compound M, with the molecular formula C(10)H(12)O(3)N(2) is formed in excellent yields. On the basis of these observations draw the structures of…arrow_forwardC9H10O2: IR absorption at 1718 cm–1. Propose a structure with data given.arrow_forward
- y-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since y-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. y-Butyrolactone shows an absorption in its IR spectrum at 1770 cm-1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of y-butyrolactone?arrow_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_forwardCompounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1. 1.Based on the information provided, determine the structure of compounds B and C. 2.Assign all peaks in 1H NMR spectrum of compounds B and C.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning