Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 13, Problem 44P
When furan and maleimide undergo a Diels–Alder reaction at 25°C, the major product is the endo adduct G. When the reaction is carried out at 90°C, however, the major product is the exo isomer H. The endo adduct isomerizes to the exo adduct when it is heated to 90°C. Propose an explanation that will account for these results.
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For a diels-alder reaction between anthracene and maleic anhydride, are the exo and endo forms of product 9,10-dihydroanthracene-9,10-ɑ,β-succinic acid anhydride different stereoisomers or are they the same molecule? Explain your answer by drawing the molecule.
Would it be favorable to get a 1,4-adduct of anthracene and maleic anhydride? Why or why not? If the 1,4-adduct of anthracene and maleic anhydride had formed, would it have different exo and endo isomers? Yes or no and why?
what is the product after these compumds undergo a diels-alder reaction
Diels–Alder reaction of a monosubstituted diene (such as CH2=CH–CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO)gives a mixture of products, but the 1,2-disubstituted product oftenpredominates. Draw the resonance hybrid for each reactant, and use thecharge distribution of the hybrids to explain why the 1,2-disubstitutedproduct is the major product.
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 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 13 - Prob. 46PCh. 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. 2LGP
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- The following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product. Account for the observation that the Diels-Alder reaction given in this problem takes place under milder conditions (at lower temperature) than the analogous Diels-Alder reaction shown in Problem 20.34.arrow_forwardBASED ON THIS EXPERIMENT: The purpose of this experiment is to perform a Diels-Alder reaction between E,E-2,4-hexadien-1-ol and maleic anhydride in a "neat" or solventless condition. The Diels-Alder reaction is a [4+2] cycloaddition that forms a six-membered ring, typically a derivative of cyclohexene. The diene, E,E-2,4-hexadien-1-ol, and the dienophile, maleic anhydride, will be mixed and ground together, resulting in a eutectic mixture. The reaction is unique as it occurs without a solvent, contributing to a "greener" experiment. After the reaction, the product will be analyzed through mass measurements, and the mechanism involves a subsequent nucleophilic acyl substitution. QUESTION: how many carbon atoms does a dienophile contribute to the Diels-Alderadduct? How many carbon atoms does a diene contribute? draw andlabel which reagent is the diene, and which is the dienophile.arrow_forwardA2 What is the inverse electron demand Diels–Alder reaction? Please pick a pair of a diene and a dienophile from the following dienes and dienophile that will undergo this type of reaction. Please show how this reaction works using Frontier Molecular Orbitals. What is the reaction product?arrow_forward
- Write a general rule that can be used to predict the major product of a Diels–Alder reaction between an alkene with an electron-withdrawing substituent and a diene with a substituent that can donate electrons by resonance depending on the location of the substituent on the diene.arrow_forwardDiels–Alder reaction of a monosubstituted diene (such as CH2=CH– CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant, and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.arrow_forwardDiels—Alder reaction of a monosubstituted diene (such as CH2 = CH – CH = CHOCH3) with a monosubstituted dienophile (such as CH2 = CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.arrow_forward
- The Diels-Alder reaction is not limited to making six-membered rings with only carbon atoms. Predict the products of the following reaction that produce rings with atoms other than carbon in them.arrow_forwardThe following compound can carry out the Diels-Alder reactionarrow_forwardWhich constitutional isomer represents the product of this Diels-Alder reaction?arrow_forward
- Complete the Diels-Alder reactions by drawing structures for the products in each question.arrow_forwardFor a diels-alder reaction between anthracene and maleic anhydride, are the exo and endo forms of product 9,10-dihydroanthracene-9,10-ɑ,β-succinic acid anhydride different stereoisomers or are they the same molecule?arrow_forwardUemura and coworkers studied a time dependent Diels-Alder reaction which first formed the endo product as the major organic product and with time produced the exo product (J. Org. Chem. 2018, 83, 9300−9304). Show the endo and exo product for the reaction below. Which is the thermodynamic product and which is the kinetic product? Explain your reasoning.arrow_forward
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