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 45P
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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Step 6: Now that you have determined the substrates and mechanism of a Diels-Alder reaction, you will learn how to recognize
when you should use the Diels-Alder reaction. In a synthesis reaction, if you are given a cyclohexene product with no other
obvious functional group transformations and an electron-withdrawing group two carbons away from the alkene, it is likely
made via the Diels-Alder reaction.
Deduce the structures of the starting materials to form the Diels-Alder adduct shown.
.....
CN
CN
Diene + Dienophile
Compounds P and Q can undergo a Diels-Alder reaction to form two
regioisomeric products R and S as shown in Figure 5.
OMe
O
C8H12O2
R
C8H12O2
S
Figure 5
Draw the chemical structures of regioisomeric compounds R and S.
Using possible resonance contributors of P and Q predict which of the two
regioisomers will be favoured in the reaction.
Using curly arrows, draw the mechanism for the reaction of P and Q to form the
dominant regioisomer you have predicted in your answer to part (ii) above.
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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- The following is an example of a hetero Diels-Alder reaction, because a noncarbon atom (in this case, an N atom) is involved in bond formation and bond breaking. Draw the curved arrows necessary to account for this transformation. OCH3 OCH3 + N- Hydroquinone, benzene, 25 °C, 90 min 86%arrow_forward4arrow_forwardA hetero Diels-Alder reaction is a variation of the Diels-Alder reaction in which one or more carbon atoms of the diene and/or the dienophile are replaced by other atoms such as oxygen or nitrogen. With this in mind, propose a mechanism consistent with the following transformation in which a multifunctional acyclic reactant produces a macrocyclic (large ring) product. 195°C. 2 Ph Ph- Ph IIarrow_forward
- A2 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_forwardThe 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_forward1,3-Butadiene is a gas at room temperature that requires a gas-handling apparatus to use in a Diels-Alder reaction. Butadiene sulfone is a convenient substitute for gaseous 1,3-butadiene. This sulfone is a solid at room temperature (mp 66°C), and when heated above its boiling point of 110°C, it decomposes by a reverse Diels-Alder reaction to give cis-1,3-butadiene and sulfur dioxide. Draw Lewis structures for butadiene sulfone and SO, then show by curved arrows the path of this reaction, which resembles a reverse Diels-Alder reaction. 140°C SO2 Butadiene sulfone 1,3-Butadiene Sulfur dioxidearrow_forward
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