Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 20, Problem 20.35P
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.
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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
0"C
Diels-Alder adduct
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.
When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 °C, an interesting Diels–Alderadduct of formula C20H14 results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and abroad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings ofanthracene reacted as a diene
Chapter 20 Solutions
Organic Chemistry
Ch. 20.1 - Prob. 20.1PCh. 20.1 - Estimate the stabilization gained as a result of...Ch. 20.2 - Predict the product(s) formed by addition of one...Ch. 20.3 - Prob. 20.4PCh. 20.3 - Prob. 20.5PCh. 20.4 - Prob. 20.6PCh. 20.5 - Prob. 20.7PCh. 20.5 - Prob. 20.8PCh. 20.5 - Prob. 20.9PCh. 20.6 - Prob. 20.10P
Ch. 20.6 - Prob. 20.11PCh. 20.6 - Prob. 20.12PCh. 20 - If an electron is added to 1,3-butadiene, into...Ch. 20 - Prob. 20.15PCh. 20 - Predict the structure of the major product formed...Ch. 20 - Predict the major product formed by 1,4-addition...Ch. 20 - Predict the structure of the major 1,2-addition...Ch. 20 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Prob. 20.21PCh. 20 - Prob. 20.22PCh. 20 - Prob. 20.23PCh. 20 - Pyridine exhibits a UV transition of the type n at...Ch. 20 - Prob. 20.25PCh. 20 - Prob. 20.26PCh. 20 - Prob. 20.27PCh. 20 - Write the frontier molecular orbital analysis for...Ch. 20 - Prob. 20.29PCh. 20 - Draw structural formulas for the products of...Ch. 20 - Propose structural formulas for compounds A and B...Ch. 20 - Under certain conditions, 1,3-butadiene can...Ch. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - The following triene undergoes an intramolecular...Ch. 20 - Prob. 20.36PCh. 20 - Prob. 20.37PCh. 20 - Prob. 20.38PCh. 20 - Prob. 20.39PCh. 20 - The Diels-Alder reaction is not limited to making...Ch. 20 - The first step in a synthesis of dodecahedrane...Ch. 20 - Bicyclo-2,5-heptadiene can be prepared in two...Ch. 20 - Prob. 20.43PCh. 20 - Prob. 20.44PCh. 20 - Following is a retrosynthetic scheme for the...Ch. 20 - Prob. 20.46PCh. 20 - Prob. 20.47PCh. 20 - Prob. 20.48PCh. 20 - Prob. 20.49PCh. 20 - Prob. 20.50PCh. 20 - What reaction presented in this chapter is...Ch. 20 - Claisen rearrangement of an allyl phenyl ether...Ch. 20 - Prob. 20.53PCh. 20 - Prob. 20.54PCh. 20 - We now continue the use of organic chemistry...Ch. 20 - Write the products of the following sequences of...
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- One step in the synthesis of dodecahedrane involves reaction of the tetraene C with dimethylacetylene dicarboxylate (D) to afford two compounds having molecular formula C16H16O4. This reaction has been called a domino Diels–Alder reaction. Identify the two products formed.arrow_forwardPredict the product(s) of the following Diels-Alder reaction. Include stereochemistry if appropriate.arrow_forwardStep 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 + Dienophilearrow_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_forwardWrite 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_forwardDraw a structural formula for the product of this Diels-Alder reaction, including the stereochemistry of the product. ÇOOEt CHO ČOOEtarrow_forward
- The following compound undergoes an intramolecular Diels-Alder reaction to give a tricyclic product. Propose a structural formula for the product. heat An intramolecular Diels-Alder adductarrow_forwardDraw and discuss the mechanism (with arrows to show electron movements) of the Diels-Alder reaction between anthracene and maleic anhydride. Draw the orientation and phases of the reacting p-orbitals showing how they overlap in a “suprafacial” geometry to form productarrow_forwardPredict the major product of the following Diels-Alder reactions with the correct regiochemistry and stereochemistry. If an enantiomer is also made, indicate the enantiomer by adding “+ EN” beside the major product. Please explain step by step.arrow_forward
- Please show all arrow pushingj mechaaisais. Thank you!arrow_forwardA very large number of Diels-Alder reactions are recorded in the chemical literature, many of which involve relatively complicated dienes, dienophiles, or both. Predict the constitution of the Diels-Alder adduct that is expected to form from the combination of diene and dienophile below. Draw the structure of the predicted product, including relevant stereochemistry when applicable. If applicable, use the Bicyclic Stamp tool and guide points to draw each structure. NH + NC CN X NC CN Click and drag to start drawing a structure.arrow_forwardA very large number of Diels-Alder reactions are recorded in the chemical literature, many of which involve relatively complicated dienes, dienophiles, or both. Predict the constitution of the Diels-Alder adduct that is expected to form from the combination of diene and dienophile below. Draw the structure of the predicted product, including relevant stereochemistry when applicable. If applicable, use the Bicyclic Stamp tool and guide points to draw each structure. Click and drag to start drawing a structure.arrow_forward
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