Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 9, Problem 28P
Compound Q has the molecular formula
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There are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers.
Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm
Isomer B: δ = 0.84 (t, 3 H), 0.86 (s, 9H), 1.22 (q, 2H) ppm
Propose a structure given the 1H and 13C NMR spectra of the unknown compound. Assign chemical shifts to corresponding hydrogen and carbon atoms
Molecular Formula: C5H10O3
Compounds 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)
Chapter 9 Solutions
Organic Chemistry
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM
9.2 What compound with molecular...Ch. 9 - Prob. 3PPCh. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - Prob. 7PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 9PPCh. 9 - PRACTICE PROBLEM 9.9 Propose a structure for...
Ch. 9 - PRACTICE PROBLEM 9.10
What is the dihedral angle...Ch. 9 - PRACTICE PROBLEM 9.11 Draw the most stable chair...Ch. 9 - Prob. 13PPCh. 9 - Prob. 14PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - Prob. 18PPCh. 9 - Prob. 19PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Given the mass spectrum in Figure 9.44 and the...Ch. 9 - Prob. 22PCh. 9 - 9.23 How many 13C NMR signals would you predict...Ch. 9 - Prob. 24PCh. 9 - 9.25 Propose structures for the compounds G and H...Ch. 9 - Prob. 26PCh. 9 - Prob. 27PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Prob. 30PCh. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 33PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 35PCh. 9 - Ethyl bromide and methoxybenzene (shown below)...Ch. 9 - 9.34 The homologous series of primary amines, ,...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.39 Propose structures for compounds E and F....Ch. 9 - Regarding compound J, C2HxCly, use the 1H NMR and...Ch. 9 - 9.38 When dissolved in , a compound (K) with the...Ch. 9 - Compound T (C5H8O) has a strong IR absorption band...Ch. 9 - Deduce the structure of the compound that gives...Ch. 9 - 9.45 Deduce the structure of the compound that...Ch. 9 - The 1H NMR spectrum of a solution of 1,...Ch. 9 - Acetic acid has a mass spectrum showing a...Ch. 9 - The 1H NMR peak for the hydroxyl proton of...Ch. 9 - The 1H NMR study of DMF (N, N-dimethylformamide)...Ch. 9 - 9.48 The mass spectra of many benzene derivatives...Ch. 9 - Prob. 52PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.2 How many 1H NMR signals would the following...Ch. 9 - 9.3. How many 1H NMR signals would...Ch. 9 - 9.4 Which of these C6H14 isomers has the greatest...Ch. 9 - 9.5 How many 13C NMR signals would be given by the...Ch. 9 - Prob. 6QCh. 9 - 9.7 What is the structure of a compound C5H12...
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- The NMR spectrum of bromocyclohexane indicates a low field signal (1H) at δ 4.16. To room temperature, this signal is a singlet, but at -75 ° C it separates into two peaks of unequal area (but totaling one proton): δ 3.97 and δ 4.64, in ratio 4.6: 1.0. How do you explain the doubling in two peaks? According to the generalization of the previous problem, what conformation of the molecule predominates (at -75 ° C)? What percentage of the molecules does it correspond to? Solve all parts otherwise down vote and hand written solutionarrow_forwardA compound (C7H14O) has a strong peak in its IR spectrum at 1710 cm–1. Its 1H NMR spectrum consists of three singlets in the ratio 9:3:2 at δ 1.0, 2.1, and 2.3, respectively. Identify the compound.arrow_forwardTreatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 20.arrow_forward
- A hydrocarbon, compound B, has molecular formula C6H6, and gave an NMR spectrum with two signals: delta 6.55 pm and delta 3.84 pm with peak ratio of 2:1. When warmed in pyridine for three hr, compound B quantitatively converts to benzene. Mild hydrogenation of B yielded another compound C with mass spectrum of m/z 82. Infrared spectrum showed no double bonds; NMR spectrum showed one broad peak at delta 2.34 ppm. With this information, address the following questions. a) How many rings are in compound C? b) How many rings are probably in B? How many double bonds are in B? c) Can you suggest a structure for compounds B and C? d) In the NMR spectrum of B, the up-field signal was a quintet, and the down field signal was a triplet. How must you account for these splitting patterns?arrow_forwardCompound A has molecular formula C5H10O. It shows three signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.1 ppm, a singlet of integral 3 at 2.14 ppm, and a quintet of integral 1 at 2.58 ppm. Suggest a structure for A and explain your reasoning.arrow_forwardIdentify the structures of isomers H and I (molecular formula C8H11N).a.Compound H: IR absorptions at 3365, 3284, 3026, 2932, 1603, and 1497 cm−1b.Compound I: IR absorptions at 3367, 3286, 3027, 2962, 1604, and 1492 cm−1arrow_forward
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- A compound has the molecular formula of CH100. It decolorizes bromine in carbon tetrachloride. The IR spectrum of the compound has a broad peak at 3500 cm and a sharp peak at 3300 cm. The 'H NMR spectrum consists of: triplet, 8 1.0 singlet, 82.4 (1H) singlet, ô 1.4 singlet, 83.4 (1H) quartet, ô 1.6 A likely structure for the compound is which of these? A) CH2=CCH=CHCH2OH CH3 B) CH3 CH3 CH2CC=CH | он CH3 CH2=CCHCH=CH2 он D) HOCH2CH2CHC=CH CH3 E) CH3CHCH2C=CCH3 | он O A O c O D Earrow_forwardThe 1H and 13C NMR spectra of compound A, C8H9Br, are shown. Propose a structure for A, and assign peaks in the spectra to your structure.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
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