Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 13, Problem 51P
Explain the product distribution below based on the polarity of the diene and dienophile, as predicted by contributing resonance structures for each.
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predict the product of the Diels-Alder reaction below, taking stereochemistry into account if relevant
Complete the following by drawing products for a and b, and also identify the diene and dienophile in each one.
Which diene and dienophile would react to give the following Diels-Alder 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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- Explain, with reference to the mechanism, why addition of one equivalent of HCl to diene A forms only two products of electrophilic addition, even though four constitutional isomers are possible.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 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_forward
- The diene below when heated,will automatically cyclize into the cyclobutene shown . Explain how this reaction is possible accounting for the stereochemical outcomesarrow_forwardDimethyl azodicarboxylate takes part in a DielsAlder reaction as a dienophile. Write the structure of the cycloaddition product of this molecule with 1,2-dimethylenecyclohexane. Knowing that this compound is formed under mild conditions, explain what favors reactivity in a Diels-Alder reaction over diene and dienophile structures.arrow_forwardThe diene lactone shown in part (a) has one electron-donating group (¬OR) and one electron-withdrawing group(C“O). This diene lactone is sufficiently electron-rich to serve as the diene in a Diels–Alder reaction.(a) What product would you expect to form when this diene reacts with methyl acetylenecarboxylate, a strong dienophile?arrow_forward
- provide the proper diene and dienophile that will result in generating the products below. Thank you!arrow_forwardComplete the following Diels-Alder reaction by drawing a structure for the product formed. Consider the resonance in the diene and dienophile and draw partial charges at correct positions. That will help you in drawing the correct product.arrow_forwardDraw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shownarrow_forward
- Give the structure of the main product of each of the following Diels-Alder reactions. Make sureto show the stereochemistry of the products when unambiguous.arrow_forwardKepone, aldrin, and chlordane are synthesized from hexachlorocyclopentadiene and other five-membered-ring compounds. Show how these three pesticides are composed of two five-membered rings.arrow_forwardGive the structures of two different alkyl bromides both of which yield the indicated alkene as the exclusive product of E2 elimination.arrow_forward
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