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- Nitriles, 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_forward3-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_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_forward
- Treatment of 3,4-dibromohexane with strong base leads to loss of 2 equivalents of HBr and formation of a product with formula C6H10. Three products are possible. Name each of the three, and tell how you would use 1H and 13CNMR spectroscopy to help identify them. How would you use UV spectroscopy?arrow_forwardWould you expect allene, H2C = C = CH2, to show a UV absorption in the 200 to 400 nm range? Explain.arrow_forwardPropose a structure consistent with following set of spectral data: C4H8Br2: IR peak at 3000–2850 cm−1; NMR (ppm):1.87 (singlet, 6 H)3.86 (singlet, 2 H)arrow_forward
- Assume that you have a compound with the formula C4H8O. a) How many double bonds and/or rings does your compound contain? b) If your compound shows an infrared absorption peak at 1715 cm-1, what functional group does it have? c) If your compound shows a single 1H NMR absorption peak at 2.1 δ, what is its structure?arrow_forwardCyclohexene has the formula C6H1o and the structure shown in Figure 4-4. When cyclohexene is treated with acid and water it forms Compound A with the formula C6H12O. When Compound A is treated with an oxidizing agent, it forms Compound B with the formula C6H100. IR spectra for Compounds A and B are shown in Figure 4-3. The best structure for A is The best for B isarrow_forwardDraw the structure for C5H10O with 1H NMR signals: δ 1.2 (s, 6H), 2.1 (bs, 1H), 5.0 (dd, 1H), 5.2 (dd, 1H), and 5.9 (dd, 1H).arrow_forward
- An oxygen containing compound shows strong Infrared radiation absorption at 1630 - 1780 cm^-1 and 3200 - 3550 cm^-1. What type of compound is it likely to be? A. An ether B. A ketone C. A carboxylic acid D. An alcohol E. An aldehydearrow_forwardDraw a structure consistent with the following set of data: a hydrocarbon with a molecular ion at m/z = 68 and IR absorptions at 3310, 3000−2850, and 2120cm−1.arrow_forwardWhat is the structure of the compound with the formula C5H12O, if it has a strong broad IR signal centered near 3330 cm-2, and the 1H-NMR spectrum is: 0.91 ppm (3H triplet) 1.19 ppm (6H singlet) 1.50 ppm (2H quartet) 2.24 ppm (1H singlet)arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning