Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 14, Problem 18P
Interpretation Introduction
Interpretation:
Out of the given compounds,
Concept introduction:
An aromatic compound is more stable than an anti-aromatic compound.
Aromatic compound has
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State if the following compounds are aromatic, non-aromatic, or anti-aromatic
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Chapter 14 Solutions
Organic Chemistry
Ch. 14 - PRACTICE PROBLEM 14.1 Provide a name for each of...Ch. 14 - Prob. 2PPCh. 14 - Prob. 3PPCh. 14 - Practice Problem 14.4 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.5 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.6 1,3,5-Cycloheptatriene is...Ch. 14 - Prob. 7PPCh. 14 - Prob. 8PPCh. 14 - Practice Problem 14.9 In 1967 R. Breslow (of...Ch. 14 - Prob. 10PP
Ch. 14 - Practice Problem 14.11 In addition to a signal...Ch. 14 - PRACTICE PROBLEM 14.12
Azulene has an appreciable...Ch. 14 - Practice Problem 14.13 (a) The -Sh group is...Ch. 14 - Practice Problem 14.14
Explain how NMR...Ch. 14 - PRACTICE PROBLEM 14.15 Four benzenoid compounds,...Ch. 14 - Prob. 16PCh. 14 - Write structural formulas and give acceptable...Ch. 14 - Prob. 18PCh. 14 - Prob. 19PCh. 14 - Prob. 20PCh. 14 - Which of the hydrogen atoms shown below is more...Ch. 14 - 14.22 The rings below are joined by a double bond...Ch. 14 - Prob. 23PCh. 14 - 14.24 (a) In 1960 T. Katz (Columbia University)...Ch. 14 - Prob. 25PCh. 14 - Prob. 26PCh. 14 - 14.27 5-Chloro-1,3-cyclopentadiene (below)...Ch. 14 - Prob. 28PCh. 14 - Furan possesses less aromatic character than...Ch. 14 - 14.30 For each of the pairs below, predict...Ch. 14 - Assign structures to each of the compounds A, B,...Ch. 14 - Prob. 32PCh. 14 - Give a structure for compound F that is consistent...Ch. 14 - Prob. 34PCh. 14 - Prob. 35PCh. 14 - A compound (N) with the molecular formula C9H10O...Ch. 14 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 38PCh. 14 - Prob. 39PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 42PCh. 14 - Compound E has the spectral features given below....Ch. 14 - Draw all of the molecular orbitals for...Ch. 14 - Prob. 1LGPCh. 14 - Prob. 2LGPCh. 14 - 3. The NMR signals for the aromatic hydrogens of...Ch. 14 - Prob. 4LGPCh. 14 - Prob. 5LGPCh. 14 - Prob. 1QCh. 14 - Which is the correct name of the compound shown?...Ch. 14 - Prob. 3QCh. 14 - Prob. 4QCh. 14 - Give the structure of a compound with the formula...Ch. 14 - Prob. 6Q
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- Azulene, an isomer of naphthalene, has a remarkably large dipole moment for a hydrocarbon (μ = 1.0 D). Explain, using resonance structures.arrow_forward2A(2) Which of the following compounds (IV-V) are aromatic, antiaromatic or neither from both. Please explain briefly in each case NO₂ N N IV -N H₂C Varrow_forwardPlease include a short explanation as well as the electron count, thanks.arrow_forward
- For each of the following structures, would you predict these molecules to possess aromaticity? Why or why not? (a) (c) (d) (a) 4 (b) 6 (c) 6 iπ electrons, antiaromatic iT electrons in each ring, aromatic TT electrons, aromatic (d) 00 8 TT electrons, antiaromaticarrow_forwardS Coronene is a polycyclic aromatic hydrocarbon. (a) How many total T electrons does it have? (b) Is that number consistent with the fact that the compound is aromatic? Explain. Coronenearrow_forwardWhich of the following structures are aromatic? CH2 I II II IV (a) I and II (b) III and IV (c) only I (d) І, II and IVarrow_forward
- 2) State if the following compounds are aromatic, non-aromatic, or anti-aromatic. (a) S: (b) ΗΝarrow_forwardConsider the following compound, which has been synthesized and characterized:(a) Assuming this molecule is entirely conjugated, do you expect it to be aromatic, antiaromatic, or nonaromatic?(b) Why was this molecule synthesized with three tert-butyl substituents? Why not makethe unsubstituted compound and study it instead?(c) Do you expect the nitrogen atom to be basic? Explain. Why doesn’t nitrogen’s lonepair overlap with the double bonds to give a total of six electrons in the pi system?(d) At room temperature, the proton NMR spectrum shows only two singlets of ratio 1:2. The smaller signal remainsunchanged at all temperatures. As the temperature is lowered to -110 °C, the larger signal broadens and separatesinto two new singlets, one on either side of the original chemical shift. At -110 °C, the spectrum consists of threeseparate singlets of areas 1:1:1. Explain what these NMR data indicate about the bonding in this molecule. How doesyour conclusion based on the NMR data agree with…arrow_forwardName these molecules and determine if they are aromatic according to Huckel's Rule X (a) (b) Aromatic? Aromatic? (c) (d) Aromatic? Aromatic?arrow_forward
- Which statement concerning the substances below is correct? A) Compound I is non-aromatic. B) Compounds II and IV are aromatic. C) Compounds I and Ill are anti-aromatic. D) Compound II is anti-aromatic.arrow_forwardWrite structural formulas for all the constitutionally isomeric compounds having the given molecular formula.(a) C4H10(b) C5H12(c) C2H4Cl2(d) C4H9Br(e) C3H9Narrow_forwardClassify the following compounds as an aromatic, antiaromatic, or nonaromatic compounds:arrow_forward
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