Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Question
Chapter 9, Problem 30P
Interpretation Introduction
Interpretation:
The structure of compound S
Concept introduction:
A few elements such as
Chemical shift is the measurement on the
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4 ) An organic compound
having molecular formula C3H7NO shows IR absorption bands
at 3413 (m), 3236 (m), 2899-3030 (m), 1667 (s), 1634 (s) and 1460 cm-1 (s). Give the
probable structure
The infrared spectrum of the compound with the mass spectrum shown below has strong absorbances at 1482 cm, 1448 cm, and 770 cm²¹,
Molecular ion peak: M = 120.
363
216
21
FIRA
$13.3
13H
105
782
15.25
2263
100 ilo
120
Reprinted courtesy of the National Institute of Standards and Technology, U.S.
Department of Commerce. Not copyrightable in the United States
Which of the following structures is consistent with the data?
A molecule of the molecular formula C5H11Br gives rise to the NMR spectrum below. When reacted with NaOH and water, it forms a product which by NMR has 2 protons 1H
at 5.4 ppm and 1H at 5.5 ppm each having a J coupling of 17 Hz. (other protons also present) The product also has an IR stretch at 1550 cm1. Provide the structures of the
starting material (1 pt) and product (2 pts)
NaOH
H20
C5H1,Br
6H
triplet
4H
quintet
1H
quintet
10
8
7
6.
4
3
1
HSP-06-347
ppm
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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- A compound (L) with the molecular formula C9H10 reacts with bromine and gives an IR absorption spectrum that includes the following absorption peaks: 3035 cm ¹(m), 3020 cm ¹(m), 2925 cm ¹(m), 2853 cm ¹(w), 1640 cm ¹1(m), 990 cm ¹(s), 915 cm ¹(s), 740 cm ¹(s), 695 cm ¹(s). The ¹H NMR spectrum of L consists of: Doublet 3.1 ppm (2H) Multiplet 5.1 ppm Multiplet 7.1 (5H) ppm Multiplet 4.8 ppm Multiplet 5.8 ppm The UV spectrum shows a maximum at 255 nm. Propose a structure for compound L. Edit Drawing harrow_forwardA molecule of the molecular formula C5H11Br gives rise to the NMR spectrum below. When reacted with NaOH and water, it forms a product which by NMR has 2 protons 1H at 5.4 ppm and 1H at 5.5 ppm each having a 3J coupling of 17 Hz. (other protons also present) The product also has an IR stretch at 1550 cm 1. Provide the structures of the starting material and product. NaOH H,0 C;H„Br 6H triplet 4H quintet 1H quintet 10 8 Ppmarrow_forwardProvide the structure of three compounds with the molecular formula C4H,O that give an absorption peak at 1600-1640 cm¹ in the infrared spectrum, but no significant peaks at 3000-3600 cm²¹ or at 1650-1750 cm-¹.arrow_forward
- 2) A compound having molecular formula C3H60 gave the following spectral data: ( 1 ) υν : λax 292 nm, εman 21 (ii) IR: 2720 cm1 (w) and 1738 cm(s) . Deduce the structure of the compound.arrow_forwardIn eachofthe following parts, a molecularformula is given. Try to deduce thestructurethat isconsistent with the infrared spectrum. There may be more than one possible answer. a. CrH9N (Hint: 1,3 disubstituted aromatic ring is present)arrow_forwardReaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G?arrow_forward
- Compounds A, B, and C are isomers with the formula C5H11Br. Their broadband proton-decoupled 13C NMR spectra are given below. Information from the DEPT 13C NMR spectra is given near each peak. Give structures for A and B. (Note: part 2 will be posted).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) Compound A has molecular formula C9H18O but shows only one singlet in the 1H-NMR spectrum. Suggest a structure for A and explain your reasoning. (b) Compound B has molecular formula C10H14. The IR, mass, 1H-NMR, and 13C-NMR speca are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for B and explain your reasoning.arrow_forward
- Treatment of anisole (CH3OC6H5) with Cl2 and FeCl3 forms P, which has peaks in its mass spectrum at m/z = 142 (M), 144 (M + 2), 129, and 127. P has absorptions in its IR spectrum at 3096–2837 (several peaks), 1582, and 1494 cm-1. Propose possible structures for P.arrow_forwardGivem this IR Spectra: Which compound is represented by this spectra? Heptanone Heptene Heptanol Heptanalarrow_forward7. (a) Explain why- (i) UV-vis is typically recorded broad absorption maxima and not single, sharp lines; (ü) ^max for is lower than that of =CH–CH= (iüi) Amax values obtained for acetone occurs at 279 nm, in n-hexane, 270 nm in ethanol, and at 265 nm in water; (iv) phenolate ion has max at 287 nm while phenol has ^max at 270 nm.arrow_forward
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