EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 15, Problem 15.81AP
Interpretation Introduction
Interpretation:
The structure of the reactive species formed in the reaction
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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(c) Diels-Alder reactions are a highly effective way to synthesise
stereospecifically fused cyclic structures.
(1) Using suitable diagrams, curly arrows and/or reaction schemes,
explain why the reaction between cyclopentadiene and maleic
anhydride favours formation of the endo product.
(ii) If the reaction in part (i) were conducted using furan instead of
cyclopentadiene, what difference would you observe in the
product/s, with respect to their stereochemistry? (No need to draw
reaction mechanisms)
(iii) Draw the stereospecific 3D structure of the product formed during
the Diels-Alder reaction below. (No need to show the reaction
mechanism)
Нeat
Br
Br
(Figure Q11ciii)
Draw relevant resonance structures for the the phencyclone reactant that explains the lower absorption frequency of the C=O group in comparison to a diels alder adduct. When drawing resonance structures show appropriate arrows, and only move one pair of electrons at a time going from one to the next; show lone pairs and charges, as appropriate. Comment in a sentence or two. Do not involve the double bonds from the benzene ring...
two positions of anthracene sometimes react more like polyenes thanlike aromatic compounds.(a) Draw a Kekulé structure that shows how the reactive positions of anthracene are the ends ofa diene, appropriate for a Diels–Alder reaction.(b) The Diels–Alder reaction of anthracene with maleic anhydride is a common organic labexperiment. Predict the product of this Diels–Alder reaction.
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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- (a) Draw a Kekulé structure that shows how the reactive positions of anthracene are the ends of a diene, appropriate for a Diels–Alder reaction.(b) The Diels–Alder reaction of anthracene with maleic anhydride is a common organic lab experiment. Predict the product of this Diels–Alder reaction.arrow_forwardPyridine (left) and pyrrole (right) are both nitrogen-containing aromatic heterocycles. They look very similar, yet have very different basicity. Which of the two compounds is more basic and why? Use resonance structures as necessary to rationalize your choice. Pyridine Pyrrolearrow_forwardRefute or Defend: Once cyclopentadiene is distilled, it can be stored for a long period of time (e.g., weeks) before using it in a Diels-Alder reactionarrow_forward
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