ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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Chapter 14, Problem 14PP
Practice Problem 14.14
Explain how
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(a) The 'H-NMR spectrum of cyclobutanone shows two signals - signal A at 3.00 ppm and signal B at 1.95 ppm. Give the multiplicity of each signal. cyclobutanone
(b) When cyclobutanone is treated with D20 and NaOD, the only signal observable in the 1H-NMR is a singlet at 2.00 ppm. Explain why this is the case. [Note: Deuterium atoms do not display signals in the TH-NMR spectrum]
13. (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.
13. (a) Compound C undergoes a reaction with SOC1₂ (or PC15) 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.
(b) Differentiate between the following:
i) COSY and NOESY
ii) COSY 90 and COSY 45
Chapter 14 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
Ch. 14 - PRACTICE PROBLEM 14.1 Provide a name for each of...Ch. 14 - Prob. 2PPCh. 14 - Prob. 3PPCh. 14 - Practice Problem 14.4 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.5 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.6 1,3,5-Cycloheptatriene is...Ch. 14 - Prob. 7PPCh. 14 - Prob. 8PPCh. 14 - Practice Problem 14.9 In 1967 R. Breslow (of...Ch. 14 - Prob. 10PP
Ch. 14 - Practice Problem 14.11 In addition to a signal...Ch. 14 - PRACTICE PROBLEM 14.12
Azulene has an appreciable...Ch. 14 - Practice Problem 14.13 (a) The -Sh group is...Ch. 14 - Practice Problem 14.14
Explain how NMR...Ch. 14 - PRACTICE PROBLEM 14.15 Four benzenoid compounds,...Ch. 14 - Prob. 16PCh. 14 - Write structural formulas and give acceptable...Ch. 14 - Prob. 18PCh. 14 - Prob. 19PCh. 14 - Prob. 20PCh. 14 - Which of the hydrogen atoms shown below is more...Ch. 14 - 14.22 The rings below are joined by a double bond...Ch. 14 - Prob. 23PCh. 14 - 14.24 (a) In 1960 T. Katz (Columbia University)...Ch. 14 - Prob. 25PCh. 14 - Prob. 26PCh. 14 - 14.27 5-Chloro-1,3-cyclopentadiene (below)...Ch. 14 - Prob. 28PCh. 14 - Furan possesses less aromatic character than...Ch. 14 - 14.30 For each of the pairs below, predict...Ch. 14 - Assign structures to each of the compounds A, B,...Ch. 14 - Prob. 32PCh. 14 - Give a structure for compound F that is consistent...Ch. 14 - Prob. 34PCh. 14 - Prob. 35PCh. 14 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 37PCh. 14 - Prob. 38PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 41PCh. 14 - Compound E has the spectral features given below....Ch. 14 - Draw all of the molecular orbitals for...Ch. 14 - Prob. 1LGPCh. 14 - Prob. 2LGPCh. 14 - 3. The NMR signals for the aromatic hydrogens of...Ch. 14 - Prob. 4LGPCh. 14 - Prob. 5LGP
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- 13. (a) Compound C undergoes a reaction with SOC12 (or PC15) to yield compound D (Molecular Formula C₁0H10OCIBr) which has the following spectral data: Compound D: IR: 1685 cm ¹; ¹H NMR: 87.84 (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_forward10aarrow_forwardCompound A has prominent infrared absorptions at 1050, 1786, and 1852 cm and shows a single absorption in the proton NMR spectrum at 8 3.00. When heated gently with methanol, compound B, C,H,O,, is obtained. Compound B has IR absorptions at 2500–3000 (broad), 1730, and 1701 cm-, and its proton NMR spectrum in D,0 consists of resonances at & 2.7 (complex splitting) and & 3.7 (a singlet) in the intensity ratio 4:3. Give the structures A and B, omitting stereochemistry.arrow_forward
- Describe the characteristic infrared absorption frequencies that would allow you to distinguish between the following pairs of compounds. (a) pentanal and pentan-2-one (b) butanamide and pentan-3-onearrow_forward14.53 Friedel-Crafts alkylation of benzene with 1-chlorobutane gave a product for which the 'H and 13C NMR spectra are shown in L Figure 14.56. The number of attached hydrogens from DEPT analysis are indicated on the 1°C NMR spectrum. Assign a structure to the product. AIC13 + CH3CH2CH2CH2CI C10H14 all CH CH3 CH2 CH3 CH C 150 100 50 Chemical shift (8, ppm) 1.7 1.6 1.5 2.7 2.6 2.5 1.3 1.2 1.1 0.9 0.8 0.7 10 9. 8 7 6. 5 4 3 2 1 Chemical shift (8, ppm)arrow_forwardCould you please help with these questions? Thank you!arrow_forward
- (c) A tri-substituted benzene possessing one bromine and two methoxy substituents exhibit three aromatic resonances at 8 6.40, 6.46, and 7.41 ppm. Identify the substitution pattern.arrow_forwardReaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed bytreatment 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 thestructure of R?arrow_forwardProvide 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_forward
- Compound Y (molecular formula C6H10) gives four lines in its 13C NMRspectrum (27, 30, 67, and 93 ppm) and the IR spectrum given here.Propose a structure for Y. Additional spectroscopy problems on alkynes are given in Chapters B and C:Infrared spectroscopy: B.4a; B.5; B.16a; B.19a; B.21a, d; B.29Nuclear magnetic resonance spectroscopy: C.12aarrow_forwardPractice Problem 13.36b Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare the following epoxide from acetylene: H" 'Et The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B C D DMP or PCC На, Pt EtBr PHCH2BR E F H H2SO4, H20, HgSO4 МСРВА (RCO3зН) Na, NH3 (/) H2, Lindlar's cat. I K TSCI, py PhBr NANH2 1) EtMgBr; 2) H30+arrow_forwardReaction 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_forward
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