Use 'H NMR spectroscopy to distinguish between the following pairs of compounds. (8 points) а. and and OCH, An unknown compound with a molecular formula of CoH1202 shows a strong IR absorption near 1740cm*. The proton NMR of the unknown is shown below. Propose the correct structure of the compound using all the information given by showing your work.

Use 'H NMR spectroscopy to distinguish between the following pairs of compounds. (8 points) а. and and OCH, An unknown compound with a molecular formula of CoH1202 shows a strong IR absorption near 1740cm*. The proton NMR of the unknown is shown below. Propose the correct structure of the compound using all the information given by showing your work.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter13: Nuclear Magnetic Resonance Spectroscopy

Section: Chapter Questions

Problem 13.17P: Following are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each...

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Following are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. (a) Propose structural formulas of compounds G, H, and I. (b) Explain why there are four lines between 0.86 and 0.90 for compound G. (c) Explain why the 2H multiplets at 1.5 and 3.5 for compound H are so complex.
Which of these choices best describes the interpretation of the following peak that may be recorded in a 'H NMR spectrum? 1.38 & (1H, heptet (7 lines)). The underlined hydrogen atom is intended to be the one producing the peak that we are interpreting. More than one choice may describe the peak very well. O (CH3)2-CH-o (CH3)2-CH-C=0 (CH3)2-CH-C=C O (CH3)2-CH-N O (CH3)2-CH-C (CH3)2-CH-Ar None of these interpretations describes this peak.
What is the structure of an unknown compound with molecular formula C6H15N that gives the following 1H NMR absorptions: 0.9 (singlet, 1 H), 1.10 (triplet, 3 H), 1.15 (singlet, 9 H), and 2.6 (quartet, 2 H) ppm?
An unknown compound has the molecular formula C7H14O, and its 1H NMR and 13C NMR spectra are shown below. Determine the structure of the unknown compound and draw it below. Note that there are no peaks above 3 ppm in the 1H NMR, and the numbers present on the 1H NMR are the integration values for each set of peaks.
Choose the structure corresponding to the given 1H and 13C NMR spectra
An unknown organic compound is isolated. The compound produces a molecular ion at m/z = 101. There is no significant M+2 peak. The IR spectrum shows peaks ~2950 cm'. It does not have any peaks above 3000, nor around 1600-1800 or 1050 cm1. The 'H-NMR and 13C-NMR spectra are shown below. What is the name of this compound (IUPAC and common name are both acceptable)? 3H 2H PPM 20 10 30 PPM 50 40
What is the structure of a compound of molecular formula C1H1402 that shows a strong IR absorption at 3150-2850 cm1 and gives the following 'H NMR absorptions: 1.4 (triplet, 6 H), 4.0 (quartet, 4 H), and 6.8 (singlet, 4 H) ppm?
Set #1: CHCHCHCH, CHOCHSCHICHI CHCHCHCHCH a b C Shown are 4 isomeric structures with the formula C5H100. Which isomer shows 3 peaks in its ¹³C-NMR spectrum, none of which is very far downfield? Set #2: CH3CH₂CH₂CCH3 CH3CH₂CH₂CH₂CH CH₂=CHCH₂CH₂CH₂OH b C a Shown are 4 isomeric structures with the formula C5H100. Which isomer shows 3 peaks in both its ¹H and 13C NMR spectra? -OH
Consider the multiplicity of the ¹H NMR peak shown below. Identify how many hydrogens are on the neighboring carbon(s). alle 1 4 7 +/- 2 5 8 Hydrogens 3 6 9 0 X C x 100
The 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.
Following are the 'H and 13C NMR spectra for each of three isomeric ketones with formula C7H14O. Determine a structure to each pair of spectra and assign each H and C. Carbon spectrum А C,H140 Carbon spectrum В C;H140 CDCI3 200 150 100 50 Proton spectrum CDC13 A C,H140 200 150 100 50 1.96 2.00 2.91 3.0 2.5 2.0 1.5 1.0 0.5 0.0 211.04 -44.79 –17.39 – 13.78 -218.40 - 38.85 –18.55
Which of these choices best describes the interpretation of the following peak that may be recorded in a 'H NMR spectrum? 3.7 8 (2H, q). The underlined hydrogen atom is intended to be the one producing the peak that we are interpreting. O-CH2CO2H O-CH,CHX2 O-CH2CH,X O-CH2CH3 None of these interpretations describes this peak.