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(a) Deduce the structure of product A, which is highly symmetrical:
The following are selected spectral data for A:
MS
IR
(b) Write a mechanism that explains the formation of A.
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Chapter 19 Solutions
Organic Chemistry
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Essential Organic Chemistry (3rd Edition)
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Chemistry: The Central Science (13th Edition)
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Fundamentals of Heat and Mass Transfer
- As we will learn in Chapter 20, reaction of (CH3)2CO with LiC ≡ CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600–3200, 3303, 2938, and 2120 cm. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?arrow_forwardAs reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600−3200, 3303, 2938, and 2120 cm−1. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?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_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_forwardStructure createdarrow_forward1,3,5,7-Cyclooctatetraene, C8H8, is an unusual hydrocarbon in that it reacts with exactly 2 equivalents of potassium to give A, C8H8K2, which can be isolated as a white solid. A exhibits a single proton NMR signal. Draw the structure of A.arrow_forward
- Identify the structures of isomers A and B (molecular formula C9H10O). Compound A: I R peak at 1742 cm−1; 1H NMR data (ppm) at 2.15 (singlet, 3 A: H), 3.70 (singlet, 2 H), and 7.20 (broad singlet, 5 H). Compound B: I R peak at 1688 cm−1; 1H NMR data (ppm) at 1.22 (triplet, 3 B: H), 2.98 (quartet, 2 H), and 7.28–7.95 (multiplet, 5 H).arrow_forwardA compound with molecular formula C7H1402 upon hydrolysis produces an alcohol and an acid. It has the following (b) NMR data : 'H-NMR (at 298 K, 600 MHz, CDC13) : 80-92 (d, 6H), 1:52 (т, 2н), 1-69 (m, 1Н), 2-04 (s, ЗH) and 4-09 (t, 2H). 13 C-NMR : 8 21-0, 22:5, 25:1, 37.4, 63·1 and 171-2 ppm DEPT provided two inverted signals. Predict the structure of the alcohol that is obtained through hydrolysis of the mentioned parent compound. Assign appropriate IR values, 'H and 13C-NMR resonances along with a mass spectral pattern for the alcohol.arrow_forwardTreatment of compound E (molecular formula C4H8O2) with excess CH3CH2MgBr yields compound F (molecular formula C6H14O) after protonation with H2O. E shows a strong absorption in its IR spectrum at 1743 cm-1. F shows a strong IR absorption at 3600–3200 cm-1. The 1H NMR spectral data of E and F are given. What are the structures of E and F?Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppmCompound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4 H), and 1.55 (singlet, 1 H) ppmarrow_forward
- Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The 1H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoningarrow_forwardA compound of formula C6H10O2 shows only two absorptions in the proton NMR: a singlet at 2.67 ppm and a singlet at2.15 ppm. These absorptions have areas in the ratio 2:3. The IR spectrum shows a strong absorption at 1708 cm-1. Proposea structure for this compound.arrow_forward(a) Draw the structure of the compound C4H8. Wave Number, cm 1 4000 3000 2500 2000 1500 1300 1200 1100 1000 900 800 700 IR 1H NMR Pom, 8 (b) Electron ionization spectrum of this compound CAH8O showed a product ion at m/z 43. Suggest a reaction mechanism for the formation of this product ion. Absorbancearrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning