Propose possible structures consistent with each set of data. Assume each compound has an sp3 hybridized C – H absorption in its IR spectrum, and that other major IR absorptions above 1500 cm are listed. a. a compound having a molecular ion at 72 and an absorption in its IR spectrum at 1725 cm−1 b. a compound having a molecular ion at 55 and an absorption in its IR spectrum at ~2250 cm−1 c. a compound having a molecular ion of 74 and an absorption in its IR spectrum at 3600–3200 cm−1

Propose possible structures consistent with each set of data. Assume each compound has an sp3 hybridized C – H absorption in its IR spectrum, and that other major IR absorptions above 1500 cm are listed. a. a compound having a molecular ion at 72 and an absorption in its IR spectrum at 1725 cm−1 b. a compound having a molecular ion at 55 and an absorption in its IR spectrum at ~2250 cm−1 c. a compound having a molecular ion of 74 and an absorption in its IR spectrum at 3600–3200 cm−1

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

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.20P

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Propose possible structures consistent with each set of data. Assume each compound has an sp3 hybridized C—H absorption in its IR spectrum, and that other major IR absorptions above 1500 cm−1 are listed. a.a compound having a molecular ion at 72 and an absorption in its IR spectrum at 1725 cm−1 b. a compound having a molecular ion at 55 and an absorption in its IR spectrum at −2250 cm−1 c.a compound having a molecular ion at 74 and an absorption in its IR spectrum at 3600−3200 cm−1
Propose a structure consistent with each set of data.a.) C9H10O2: IR absorption at 1718 cm−1 b.) C9H12: IR absorption at 2850–3150 cm−1
Compounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1. 1.Based on the information provided, determine the structure of compounds B and C. 2.Assign all peaks in 1H NMR spectrum of compounds B and C.
Treatment of compound E (molecular formula C4H8O2) with excessCH3CH2MgBr yields compound F (molecular formula C6H14O) afterprotonation with H2O. E shows a strong absorption in its IR spectrum at1743 cm−1. F shows a strong IR absorption at 3600−3200 cm−1. The 1HNMR spectral data of E and F are given. What are the structures of E andF?Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppm Compound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4H), and 1.55 (singlet, 1 H) ppm
Propose a structure consistent with each set of data. C10H14: IR absorptions at 3150–2850, 1600, and 1500 cm−1
Propose a structure consistent with each set of spectral data: a.C6H14O: IR peak at 3600−3200 cm−1; NMR (ppm): 0.8 (triplet, 6 H) 1.5 (quartet, 4 H) 1.0 (singlet, 3 H) 1.6 (singlet, 1 H) b.C6H14O: IR peak at 3000−2850 cm−1; NMR (ppm): 1.10 (doublet, relative area = 6) 3.60 (septet, relative area = 1)
Compound B has molecular formula C9H12. It shows five signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.22 ppm, a septet of integral 1 at 2.86 ppm, a singlet of integral 1 at 5.34 ppm, a doublet of integral 2 at 6.70 ppm, and a doublet of integral 2 at 7.03 ppm. The 13C-NMR spectrum of B shows six unique signals (23.9, 34.0, 115.7, 128.7, 148.9, and 157.4). Identify B and explain your reasoning.
A hydrocarbon, compound B, has molecular formula C6H6, and gave an NMR spectrum with two signals: delta 6.55 pm and delta 3.84 pm with peak ratio of 2:1. When warmed in pyridine for three hr, compound B quantitatively converts to benzene. Mild hydrogenation of B yielded another compound C with mass spectrum of m/z 82. Infrared spectrum showed no double bonds; NMR spectrum showed one broad peak at delta 2.34 ppm. With this information, address the following questions. a) How many rings are in compound C? b) How many rings are probably in B? How many double bonds are in B? c) Can you suggest a structure for compounds B and C? d) In the NMR spectrum of B, the up-field signal was a quintet, and the down field signal was a triplet. How must you account for these splitting patterns?
Treatment of compound D with LiAlH4 followed by H2O forms compound E. D shows a molecular ion in its mass spectrum at m/z = 71 and IR absorptions at 3600–3200 and 2263 cm–1. E shows a molecular ion in its mass spectrum at m/z = 75 and IR absorptions at 3636 and 3600–3200 cm–1. Propose structures for D and E from these data and the given 1H NMR spectra.
Propose a structure consistent with each set of data Compound A: Molecular formula: C8H10OIR absorption at 3150−2850 cm−11H NMR data: 1.4 (triplet, 3 H), 3.95 (quartet, 2 H), and 6.8–7.3(multiplet, 5 H) ppm
Treatment 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) ppm
These are the 1H RMN and IR spectrums of an A compound with formula C10H13NO2. When A reacts with NaOH in water and heat, B compound is formed, with formula C10H11NO. What are the structures of A and B?