Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 14, Problem 3PP
Interpretation Introduction
Interpretation:
The reason that the structures for benzene having alternate long and short bonds violate a basic principle of resonance theory is to be explained.
Concept introduction:
Resonating structures exhibit the movement of electrons and are drawn by moving the electrons. The position of atoms present in the compound does not change. Resonating structures describes the delocalization of electrons within molecules. It compares and contrasts two or more possible Lewis structures that can represent a particular molecule. Resonance structures are used when one Lewis structure for a single molecule cannot fully describe the bonding that takes place between neighboring atoms relative to the empirical data for the actual bond lengths between those atoms. The net sum of valid resonance structures is defined as a resonance hybrid, which represents the overall delocalization of electrons within the molecule. A molecule that has several resonance structures is more stable than one with fewer.
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Practice Problem 13.37a
Draw the major organic product of the following reaction sequence.
1) RCO3H
2) MeMgBr
3) H20
Aromaticity
On the basis of Huckel's rule, label the following molecules as aromatic, nonaromatic or antiaromatic. Share your answers and comment on two other students' postings - have they
correctly labeled the molecules?
(a)
(c)
(e)
anthracene
[12]annulene
azulene
(b)
(d)
[10]annulene
[14]annulene
S-indacene
Practice Problem 13.37f
Draw the major organic product of the following reaction sequence.
.CI
1) Mg, diethyl ether
2)
3) H20
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 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 37PCh. 14 - Prob. 38PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 41PCh. 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. 5LGP
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