Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 9, Problem 7PP
PRACTICE PROBLEM 9.7
The relative chemical shifts of the doublet and triplet of 1,1,2-trichloroethane (Fig. 9.4) and 1,1,2,3,3-pentachloropropane (Fig. 9.12) are reversed. Explain this.
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Part 3B Set 1. Can IR spectroscopy be used to differentiate between the two compounds? Briefly explain why or why not. What significant absorptions would be observed in the IR spectrum?
Deduce the strcuture of compound E2 for which spectral data is provided. Make assignment for all of the spectral peaks which you can by writing directly on the spectral traces. Make these assignments in terms of structures of fragments or functionalities whenever possible.
Draw the proposed structure. If you can deduce two or more strcutures consistent with the data provided, indicate all of these structures and indicate your preference with any reasons you have for your choice.
Predict the characteristic infrared absorptions of the functional groups in the following molecules. pentanamide
Chapter 9 Solutions
Organic Chemistry
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM 9.2 What compound with molecular...Ch. 9 - PRACTICE PROBLEM 9.3
Using the method of Section...Ch. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 8PPCh. 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. 12PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 14PPCh. 9 - Prob. 15PPCh. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Prob. 19PPCh. 9 - How many 1H NMR signals (not peaks) would you...Ch. 9 - How many 13C NMR signals would you predict for...Ch. 9 - Prob. 22PCh. 9 - Prob. 23PCh. 9 - Prob. 24PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Compound S (C8H16) reacts with one mole of bromine...Ch. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 30PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 32PCh. 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 - 9.36 Propose structures for compounds E and F....Ch. 9 - 9.37 Use the NMR and IR data below to propose a...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 - Prob. 40PCh. 9 - Deduce the structure of the compound that gives...Ch. 9 - Deduce the structure of the compound that gives...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. 49PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...
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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
- Given the spectral data included in this problem and that the molecular formula is C4H5O2, determine the most likely structure using your understanding of carboxylic acid properties and spectroscopy. Indicate the following on each graph by: a.) labeling the IR spectrum with the relevant bond stretches, b.) indicating the relevant mass spectrum molecular ion and any relevant fragments, c.) providing a legible structure of the final product and name the compound.arrow_forwardPredict the characteristic infrared absorptions of the functional groups in the following molecules. ) pent-1-ynearrow_forwardUse the functional group of the compound with the following IR absorption spectrum.arrow_forward
- Determine the structure. Note that for the 13C data, multiplicity is given. So a CH3 group would be a quartet (n+1) and a CH2 group would be a triplet, etcarrow_forwardPredict the characteristic infrared absorptions of the functional groups in the following molecules. (a) ethyl acetate (b) pentanamidearrow_forwardWhat information can be obtained from the UV-visible spectrum for compound 1 and 2?arrow_forward
- Given the IR spectrum for 2-Naphthyl-Butylether identify and label the peaks with the types of bonds.arrow_forwardUsing the Frost Circle method to outline the molecular orbitals of cyclobutadiene, and identify whether it is aromatic, antiaromatic or non-aromatic. Explain.arrow_forwardUsing the attached infrared spectroscopy spectrum for the compound Tetrahydrofuran, identify the functional group and any observed characteristic absorbtions in cm-1. Compare with the attached roadmap for interpreting IR spectra.arrow_forward
- Deduce the structure of compound E1 for which spectral data is provided. Make assignment of the spectral peaks which you can by writing directly on the spectral traces. Make these assignments in terms of structures of fragments or functionalities whenever possible. Draw the proposed structure. If you can deduce two or more structures consistent with the data provided, include all of these structures and indicate your preference with any reasons you have for your choice.arrow_forwardProvide a brief justification for the identification of 1-propanol, hexane, benzyl alcohol, 1-hexanol and ethyl benzoate based on 2-3 key bands in each spectrum, which suggest the presence (or absence) of specific functional groups. You do not need to identify all the bands in the spectra -that would be almost impossible. If the bands are too similar (or in addition, to strengthen your discussion), you could look the IR spectra of the compounds in a database and see whether the IR of the unknowns can be identified this way.arrow_forwardDr. Danahy has never forgotten nor forgiven the molecule below from her undergraduate research. The extensive hydrogen bonding within the molecule (intramolecular) caused it to appear as two different compounds in the 1H NMR spectrum (no need to worry about why), even though it was only one compound! The true structure was revealed when she followed a colleague’s suggestion: to dissolve the compound in methanol rather than chloroform. In terms of hydrogen bonding, how might the compound behave in methanol versus chloroform?arrow_forward
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IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY