Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 13, Problem 13PP
Interpretation Introduction
Interpretation:
Theproducts formed from Diels Alder reaction of (2Z,4Z)-hexa-2,4-diene with methyl propenoate are to be determined.
Concept introduction:
A Diels Alder reaction is one between a conjugate diene and a reactant containing a double bond (dienophile) to form a product. The product is called adduct.
Diels Alder reactions are highly stereospecific. The configuration of the dienophile is retained in the product and the reaction is a syn addition reaction.
The dienes react with dienophiles in cis forms rather than trans forms.
Endo and exo refer to the orientation of the dienophile and its electron-withdrawing group when it reacts with a diene in a Diels Ander reaction.
Endo is favored in the transition state of aDiels Ander reaction because it has a lower energy.
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Students have asked these similar questions
Of the three 1,4-diphenyl-1,3-butadiene isomers (E,E or E,Z or Z,Z) indicate the most suitable diene that can be used as a reactant in a Diels-Alder reaction. Explain your choice.
14. Please write the major product for each following Diels-Alder reaction. Explain why they are formed by using Frontier Molecular Orbital theory.
(a) 1-(diethylamino)-1,3-butadiene + acrylate
(b) 2-ethoxy-1,3-butadiene + acrylate
Moreover, draw Molecular Orbitals of 1-(diethylamino)-1,3-butadiene, 2-ethoxy-1,3-butadiene & acrylate. In addition, mark energy levels and predict the products by using FMO theory.
Following is an example of a type of reaction known as a Diels-Alder reaction
1,3-Pentadiene
Ethylene
3-Methylcyclohexene
(a racemic mixture)
The Diels-Alder reaction between a diene and an alkene is quite remarkable in that it is
one of the few ways that chemists have to form two new carbon-carbon bonds in a single
reaction. Given what you know about the relative strengths of carbon-carbon sigma and
pi bonds, would you predict the Diels-Alder reaction to be exothermic or endothermic?
Explain your reasoning.
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - Prob. 1PPCh. 13 - Prob. 2PPCh. 13 - Prob. 3PPCh. 13 - Practice Problem 13.4 From each set of resonance...Ch. 13 - Practice Problem 13.5 The following enol (an...Ch. 13 - Prob. 6PPCh. 13 - Practice Problem 13.7
Two compounds, A and B, have...Ch. 13 - Prob. 8PPCh. 13 - Prob. 9PPCh. 13 - Prob. 10PP
Ch. 13 - Prob. 11PPCh. 13 - Prob. 12PPCh. 13 - Prob. 13PPCh. 13 - Prob. 14PPCh. 13 - Prob. 15PPCh. 13 - Practice Problem 13.16
Diels–Alder reactions also...Ch. 13 - Prob. 17PPCh. 13 - Prob. 18PCh. 13 - What product would you expect from the following...Ch. 13 - Prob. 20PCh. 13 - Prob. 21PCh. 13 - Provide the reagents necessary for each of the...Ch. 13 - Prob. 23PCh. 13 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - When 1-pentene reacts with N-bromosuccinimide...Ch. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - 13.31 Provide a mechanism that explains formation...Ch. 13 - 13.32 Provide a mechanism that explains formation...Ch. 13 - Treating either 1-chloro-3-methyl-2-butene or...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Although both 1-bromobutane and 4-bromo-1-butene...Ch. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Prob. 44PCh. 13 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 13 - Prob. 47PCh. 13 - Prob. 48PCh. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Explain the product distribution below based on...Ch. 13 - Mixing furan (Problem 13.44) with maleic anhydride...Ch. 13 - Prob. 53PCh. 13 - Prob. 54PCh. 13 - Prob. 1LGPCh. 13 - Prob. 2LGPCh. 13 - Prob. 1QCh. 13 - Prob. 2QCh. 13 - Prob. 3QCh. 13 - Prob. 4QCh. 13 - Prob. 5Q
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