EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 15, Problem 15.79AP
Interpretation Introduction
Interpretation:
An explanation regarding the salt-like behavior of
Concept introduction:
Most of the organic structures cannot be represented using a single Lewis structure. Therefore, there exists more than one Lewis structure for representing a molecule or ion. These structures are known as resonance structures. The delocalization of electrons results in the formation of resonance structure. The curved-arrow notation traces the flow of the electrons in a compound. This notation is used to derive the resonance structure.
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Treatment of cis-4-bromocyclohexanol with HO− affords compound Aand cyclohex-3-en-1-ol. Treatment of trans-4-bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and Bcontain different functional groups and are not isomers of each other.Propose structures for A and B and offer an explanation for theirformation.
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• You do not have to consider stereochemistry.
•You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
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?
Sn th
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Following is the structural formula of the principal sex pheromone of the Douglas fir tussock moth (Orgyia pseudotsugata), a severe defoliant of the fir trees of western North America.
Several syntheses of this compound have been reported, one of which is shown:
O. _OH
Br
(Z)-6-Heneicosene-11-one
alkyl bromide 1
hemiacetal 1
alkyl bromide 2
Br
This synthesis involves the following steps:
1. Alkyl bromide 2 reacts with triphenylphosphine and butyllithium to form ylide 1;
2. Hemiacetal 1 is in equilibrium with aldehyde 2;
3. Aldehyde 2 reacts with ylide 1 to form oxaphosphetane 3;
4. Oxaphosphetane 3 expels triphenylphosphine oxide to form alkene 4 (the alkene is primarily formed in the desired Z configuration);
5. Alkene 4 is oxidized with PCC to form aldehyde 5;
6. Alkyl bromide 1 reacts with magnesium and ether to form Grignard reagent 6;
7. Grignard reagent 6 adds to aldehyde 5 to form tetrahedral intermediate 7;
8. Tetrahedral intermediate 7 reacts with dilute aqueous acid to form…
Chapter 15 Solutions
EBK ORGANIC CHEMISTRY
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Prob. 15.6PCh. 15 - Prob. 15.7PCh. 15 - Prob. 15.8PCh. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Prob. 15.19PCh. 15 - Prob. 15.20PCh. 15 - Prob. 15.21PCh. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - Prob. 15.41PCh. 15 - Prob. 15.42APCh. 15 - Prob. 15.43APCh. 15 - Prob. 15.44APCh. 15 - Prob. 15.45APCh. 15 - Prob. 15.46APCh. 15 - Prob. 15.47APCh. 15 - Prob. 15.48APCh. 15 - Prob. 15.49APCh. 15 - Prob. 15.50APCh. 15 - Prob. 15.51APCh. 15 - Prob. 15.52APCh. 15 - Prob. 15.53APCh. 15 - Prob. 15.54APCh. 15 - Prob. 15.55APCh. 15 - Prob. 15.56APCh. 15 - Prob. 15.57APCh. 15 - Prob. 15.58APCh. 15 - Prob. 15.59APCh. 15 - Prob. 15.60APCh. 15 - Prob. 15.61APCh. 15 - Prob. 15.62APCh. 15 - Prob. 15.63APCh. 15 - Prob. 15.64APCh. 15 - Prob. 15.65APCh. 15 - Prob. 15.66APCh. 15 - Prob. 15.67APCh. 15 - Prob. 15.68APCh. 15 - Prob. 15.69APCh. 15 - Prob. 15.70APCh. 15 - Prob. 15.71APCh. 15 - Prob. 15.72APCh. 15 - Prob. 15.73APCh. 15 - Prob. 15.74APCh. 15 - Prob. 15.75APCh. 15 - Prob. 15.76APCh. 15 - Prob. 15.77APCh. 15 - Prob. 15.78APCh. 15 - Prob. 15.79APCh. 15 - Prob. 15.80APCh. 15 - Prob. 15.81APCh. 15 - Prob. 15.82APCh. 15 - Prob. 15.83APCh. 15 - Prob. 15.84APCh. 15 - Prob. 15.85APCh. 15 - Prob. 15.86AP
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