Concept explainers
(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.
Want to see the full answer?
Check out a sample textbook solutionChapter 19 Solutions
Organic Chemistry
Additional Science Textbook Solutions
Anatomy & Physiology (6th Edition)
Genetic Analysis: An Integrated Approach (3rd Edition)
Campbell Essential Biology (7th Edition)
Applications and Investigations in Earth Science (9th Edition)
Chemistry: An Introduction to General, Organic, and Biological Chemistry (13th Edition)
Microbiology: An Introduction
- 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_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_forwardDeduce the structures of compounds A and B, two of the major components of jasmine oil, from the given data. Compound A: C9H10O2; IR absorptions at 3091–2895 and 1743 cm-1; 1H NMR signals at 2.06 (singlet, 3 H), 5.08 (singlet, 2 H), and 7.33 (broad singlet, 5 H) ppm. Compound B: C14H12O2; IR absorptions at 3091–2953 and 1718 cm-1; 1H NMR signals at 5.35 (singlet, 2 H) and 7.26–8.15 (multiplets, 10 H) ppm.arrow_forward
- A 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_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_forwardBenzonitrile (C6H5CN) is reduced to two different products depending on the reducing agent used. Treatment with lithium aluminum hydride followed by water forms K, which has a molecular ion in its mass spectrum at 107 and the following IR absorptions: 3373, 3290, 3062, 2920, and 1600 cm-1. Treatment with a milder reducing agent forms L, which has amolecular ion in its mass spectrum at 106 and the following IR absorptions: 3086, 2820, 2736, 1703, and 1600 cm-1. L shows fragments in its mass spectrum at m/z = 105 and 77. Propose structures for K and L and explain how you arrived at your conclusions.arrow_forwardAddition of mesitylene to the strongly acidic solvent HF / SbF5 at -45 °C gives a new species which shows a 1H-NMR resonance at δ 4.67 (2H). Draw the structure of this species.arrow_forward
- Provide a structure for the compound C,HN, using the given information. IR: 3281 cm-1 'H NMR: 8 1.1 (8H, t, J = 7 Hz), 8 2.66 (4H, q, J = 7 Hz), 8 2.83 (4H, s). (Hint: The triplet at 8 1.1 conceals another broad resonance that contributes to the integral.) Draw the structure for C,HN,. 16 2arrow_forward13. (a) Compound C undergoes a reaction with SOC12 (or PCls) to yield compound D (Molecular Formula C₁0H₁0OCIBr) which has the following spectral data: Compound D: IR: 1685 cm¹; ¹H NMR: 8 7.84 (d, J = 8 Hz, 2H), 7.60 (d, J = 8 Hz, 2H), 3.65 (t, J = 7 Hz, 2H), 3.18 (t, J = 7 Hz, 2H), 2.25 (pentet, J = 7 Hz, 2H) ppm; ¹³C NMR: d 28, 36, 45, 128, 130, 133, 137, 197 ppm; EI MS m/z: 200, 198(1:1), 185, 183 (1:1). Identify compound C from the spectral data of compound B and justify your observation.arrow_forwardAcid-catalyzed hydrolysis of HOCH2CH2C(CH3)2CN forms compound A (C6H10O2). A shows a strong peak in its IR spectrum at 1770 cm-1 and the following signals in its 1H NMR spectrum: 1.27 (singlet, 6 H), 2.12 (triplet, 2 H), and 4.26 (triplet, 2 H) ppm. Draw the structure for A and give a stepwise mechanism that accounts for its formation.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning