Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 12.18, Problem 20P
Give an explanation for each of the following observations:
Compound A has six
electrons but is not
Compound B has six
Compound C has
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(a) Compound A has molecular formula C5H10O. It shows three signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.1 ppm, a singlet of integral 3 at 2.14 ppm, and a quintet of integral 1 at 2.58 ppm. Suggest a structure for A and explain your reasoning.
(b) Compound B has molecular formula C8H6O2. The IR, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for B and explain your reasoning.
(c) Compound C has molecular formula C5H8O. The IR, mass, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for C and explain your reasoning.
Following are 1H-NMR spectra for compounds B (C6H12O2) and C (C6H10O). Upon warming in dilute acid, compound B is converted to compound C. Deduce the structural formulas for compounds B and C.
Which of the following are consistent with the requirements for aromaticity?I. A system with delocalized p electrons in a ring.II. 4n p electrons in the ring.III. All the ring atoms must be carbons.IV. (4n + 2) p electrons in the ring.
Give the answer why.
Chapter 12 Solutions
Organic Chemistry - Standalone book
Ch. 12.2 - Write structural formulas for toluene (C6H5CH3)...Ch. 12.3 - Prob. 2PCh. 12.5 - Prob. 3PCh. 12.5 - Prob. 4PCh. 12.6 - Prob. 5PCh. 12.6 - Chrysene is an aromatic hydrocarbon found in coal...Ch. 12.8 - Prob. 7PCh. 12.9 - As measured by their first-order rate constants,...Ch. 12.9 - Give the structure of the principal organic...Ch. 12.9 - Prob. 10P
Ch. 12.10 - Prob. 11PCh. 12.11 - Prob. 12PCh. 12.12 - Prob. 13PCh. 12.13 - Prob. 14PCh. 12.13 - Prob. 15PCh. 12.15 - The regioselectivity of Birch reduction of...Ch. 12.16 - Prob. 17PCh. 12.17 - Both cyclooctatetraene and styrene have the...Ch. 12.17 - Prob. 19PCh. 12.18 - Give an explanation for each of the following...Ch. 12.19 - Prob. 21PCh. 12.19 - What does a comparison of the heats of combustion...Ch. 12.20 - Prob. 23PCh. 12.20 - Prob. 24PCh. 12.20 - Prob. 25PCh. 12.20 - Prob. 26PCh. 12.20 - Prob. 27PCh. 12.20 - Prob. 28PCh. 12.21 - Prob. 29PCh. 12.21 - Prob. 30PCh. 12.22 - Prob. 31PCh. 12.22 - Prob. 32PCh. 12 - Write structural formulas and give the IUPAC names...Ch. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - Acridine is a heterocyclic aromatic compound...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - Evaluate each of the following processes applied...Ch. 12 - Prob. 43PCh. 12 - Prob. 44PCh. 12 - Prob. 45PCh. 12 - Prob. 46PCh. 12 - Anthracene undergoes a DielsAlder reaction with...Ch. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - The relative rates of reaction of ethane, toluene,...Ch. 12 - Both 1,2-dihydronaphthalene and...Ch. 12 - Prob. 52PCh. 12 - Prob. 53PCh. 12 - Prob. 54PCh. 12 - Prob. 55PCh. 12 - Prob. 56PCh. 12 - Each of the following reactions has been described...Ch. 12 - Prob. 58PCh. 12 - A compound was obtained from a natural product and...Ch. 12 - Prob. 60PCh. 12 - Suggest reagents suitable for carrying out each of...Ch. 12 - Prob. 62PCh. 12 - Prob. 63DSPCh. 12 - Prob. 64DSPCh. 12 - Prob. 65DSPCh. 12 - Prob. 66DSP
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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
- 1, 6-Methanonaphthalene has an interesting 1H NMR spectrum in which the eight hydrogens around the perimeter absorb at 6.9 to 7.3 δ, while the two CH2 protons absorb at -0.5 δ. Tell whether it is aromatic, and explain its NMR spectrum.arrow_forwardCompound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardCompound A has molecular formula C5H10O. It shows three signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.1 ppm, a singlet of integral 3 at 2.14 ppm, and a quintet of integral 1 at 2.58 ppm. Suggest a structure for A and explain your reasoning.arrow_forward
- Four isomers A-D with the formula C5H12O exhibit different reactivity patterns as indicated below. Isomer A reacts with PCC and CrO3 to provide identical products. Isomer B reacts with PCC and CrO3 to provide different products. Isomers C and D do not react with either PCC or CrO3. Isomers A, B, and C readily react with NaH but D does not show any reactivity with NaH. The 1H NMR splitting patterns for these isomers are as follows. Isomer A: δ 0.91 (d, 3H), 0.90 (d, 3H), 1.18 (d, 3H), 1.92 (dqq, 1H), 3.38 (dq, 1H), 3.58 (bs, 1H). Isomer B: δ 1.25 (s, 9H), 3.45 (s, 2H), 3.65 (bs, 1H). Isomer C: δ 0.90 (t, 3H), 1.44 (q, 2H), 1.24 (s, 6H), 3.65 (bs, 1H). Isomer D: δ 1.10 (t, 3H), 1.13 (d, 6H), 3.19 (septet, 1H), 3.50 (q, 2H). Based on all of this information, provide the structures of A-D. (Note: If there is a chiral center on any of these molecules, assume the stereochemistry as “R”. dqq=doublet of a quartet of a quartet, bs=broad singlet)arrow_forwardCompound B has molecular formula C9H10. The IR spectrum is shown below. The 1H-NMR spectrum shows a multiplet at 7.2 ppm integrating to 4H, a triplet at 2.9 ppm integrating to 4H, and a triplet at 2.1 ppm integrating to 2 H. Suggest a structure for B and explain your reasoningarrow_forwardCompound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 î disappears when D2O is added.arrow_forward
- A chemist isolated an aromatic compound with molecular formula C6H4Br2. He treated this compound with nitric acid and sulfuric acid and isolated threedifferent isomers, in different amounts, with molecular formula C6H3Br2NO2. What was the structure of the original compound?arrow_forwardDraw the molecular structure of an aromatic compound with a molecular formula of C9H12. There are 9 hydrogen singlelets at 2.5 ppm and 3 hydrogen singlelets at 6.65 ppm.arrow_forwardWhy isn't this compound aromatic? Doesn't it fit the 4n+2 rule where there is 6 pi electrons? Or is it not planar, which is why it is not aromatic?arrow_forward
- Compound P has molecular formula C5H9C102. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forwardPropose a structure given the 1H and 13C NMR spectra of the unknown compound. Assign chemical shifts to corresponding hydrogen and carbon atoms Molecular Formula: C5H10O3arrow_forwardCompound 2 has molecular formula C6H12. It shows three signals in the 1H-NMR spectrum, one at 0.96 ppm, one at 2.03 ppm, and one at 5.33 ppm. The relative integrals of these three signals are 3, 2, and 1, respectively. Provide structure for compound 2, explain how you reached your conclusion.arrow_forward
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