Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 9, Problem 40P
Regarding compound J, C2HxCly, use the 1H NMR and IR data below to propose a stereochemical formula that is consistent with the data.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
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?
This compound, (C10H1002), shows strong, sharp absorption between 1700 and 1720 cm, and strong, broad absorption over the region 2500-
3000 cm. Given this information and the following NMR data, please draw the structure of the compound in the box below.
H-NMR: 2.34 ppm, s(3H); 6.38 ppm, d(1H); 7.18 ppm, d(1H); 7.44 ppm, d(2H); 7.56 ppm, d(2H); 12.0, s(1H)
19C-NMR: 167.82; 143.82; 139.96; 131.45; 129.37; 127.83; 111.89; 21.13
As we will learn in Chapter 17, 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?
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...
Additional Science Textbook Solutions
Find more solutions based on key concepts
a. Draw the most stable conformation of pentane for rotation about the C-2C-3 bond. b. Draw the least stable co...
Essential Organic Chemistry (3rd Edition)
1.14 Classify each of the following as a pure substance or a mixture. If a mixture, indicate whether it is homo...
Chemistry: The Central Science (14th Edition)
1.14 Classify each of the following as a pure substance or a mixture. If a mixture, indicate whether it is homo...
Chemistry: The Central Science (13th Edition)
Predict the major product for each of the following reactions:
Organic Chemistry As a Second Language: Second Semester Topics
The products of combustion from a burner are routed to an industrial application through a thin-walled metallic...
Fundamentals of Heat and Mass Transfer
23. Give the symbol and name for (a) an isotope with a mass number of 37 and an atomic number of 17 and (b) an ...
Chemistry For Changing Times (14th Edition)
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Treatment of compound C (molecular formula C4H8O) with C6H5MgBr, followed by H2O, affords compound D (molecular formula C10H14O). Compound D has a strong peak in its IR spectrum at 3600–3200 cm−1. The 1H NMR spectral data of C and D are given. What are the structures of C and D? Compound C signals at 1.3 (singlet, 6 H) and 2.4 (singlet, 2 H) ppm Compound D signals at 1.2 (singlet, 6 H), 1.6 (singlet, 1 H), 2.7 (singlet, 2 H), and 7.2 (multiplet, 5 H) ppmarrow_forward2) A compound with molecular formula C4H8O2 gives an H-NMR spectrum with a 2H quartet at 4.1 ppm, a 3H singlet at 2.0 ppm, and a 3H triplet at 1.3 ppm. Calculate degrees of unsaturation, sketch the spectrum below, propose a reasonable structure for the compound, and add all of the same details in the example provided for problem #1 above.arrow_forward2H зн 3H 2H 2H 2H 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 PPM Determine the structure of A based on these spectra. Indicate clearly the signals for each type of protons for NMR analysis. Compound A gives NMR and IR spectra has the formula C3H1403arrow_forward
- The 'H NMR spectrum of a compound with formula C;H40 gives three signals. Which of these structures is a possible one for this compound? O 2-Heptanone O 3-Heptanone O 2,4-Dimethyl-3-pentanone 2,2-Dimethyl-3-pentanone • Two of these choices.arrow_forward3. Propose a structure for an organic compound with molecular formula C3H1404 given the following 'H NMR and IR spectra. Draw the structure only, no need to interpret the spectra. 1H NMR Spectrum IR Spectrum Triplet Singlet d (6H) 8 (4H) 8 (4H) 1740 cm1 Quartetarrow_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
- The compound with the closed formula C4H9Br gives the following 1H NMR data. Write the clear formula of the compound with reasons. 1.0 ppm (triplet, 3 H); 1.7 ppm (dublet, 3H); 1.8 ppm (multiplet, 2H); 4.2 ppm (multiplet, 1H)arrow_forwardDraw the structure of an ether with formula C5H12O2 that fits the following NMR spectrum.arrow_forwardAn unknown compound X has the molecular formula C6H140. Compound at 3000 cm. The 'H NMR spectral data of compound X is given below. W Here PPM values are given in delta symbol. absorption 8 ratio triplet 1.0 3 singlet 1.1 quartet singlet 1.5 3.5 3 623 6 O C) III O A) I O D) IV O B) II I 11 OH t III IVarrow_forward
- An alkyl halide reacts with an alkoxide ion to form a compound whose 1H NMR spectrum is shown here. Identify the alkyl halide and the alkoxide ion.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_forwardHow would you use NMR (either 13C or 1H) to distinguish between the following pairs of isomers?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY