ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
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Chapter 15, Problem 15.35SP
Furan and malemide undergo a Diels-Alder reaction at 25 °C to give the endo isomer of the product. When the reaction takes place at 90 °C, however, the major product is the exo isomer. Further study shows that the endo isomer of the product isomenzes to the exo isomer at 90 °C.
- a. Draw and label the endo and exo isomers of the Dieis-Alder adduct of furan and maleimide.
- b. Which isomer of the product would you usually expect from this reaction? Explain why this isomer is usually favored.
- c. Examine your answer to (b) and determine whether this answer applies to a reaction that is kinetic ally controlled or one that is
thermodynamically controlled, or both. - d. Explain why the endo isomer predominates when the reaction takes place at 25 °C and why the exo isomer predominates at 90 °C.
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Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electrons-pushing arrows for the following reaction or mechanistic step(s).
Chapter 15 Solutions
ORGANIC CHEMISTRY
Ch. 15.2 - Prob. 15.1PCh. 15.2 - Prob. 15.2PCh. 15.2 - Prob. 15.3PCh. 15.4 - Prob. 15.4PCh. 15.4 - Prob. 15.5PCh. 15.5 - Treatment of an alkyl halide with AgNO3 in alcohol...Ch. 15.5 - Propose a mechanism for each reaction, showing...Ch. 15.6 - When Br2 is added to buta-1,3-diene at 15 C, the...Ch. 15.7 - Prob. 15.9PCh. 15.7 - When N-bromosuccinimide is added to hex-1-ene in...
Ch. 15.7 - Prob. 15.11PCh. 15.9 - Addition of 1-bromobut-2-ene to magnesium metal in...Ch. 15.10 - Show how you might synthesize the following...Ch. 15.11 - Predict the products of the following proposed...Ch. 15.11 - Prob. 15.15PCh. 15.11A - Prob. 15.16PCh. 15.11B - Prob. 15.17PCh. 15.11B - Predict the products of the following Diels-Alder...Ch. 15.12C - Prob. 15.19PCh. 15.12C - Prob. 15.20PCh. 15.13C - Prob. 15.21PCh. 15.13D - Using the examples in Table15-2 to guide you,...Ch. 15.14 - Phenolphthalein is an acid-base indicator that is...Ch. 15 - Prob. 15.24SPCh. 15 - Prob. 15.25SPCh. 15 - Show how the reaction of an allylic halide with a...Ch. 15 - Prob. 15.27SPCh. 15 - A solution was prepared using 0.0010 g of an...Ch. 15 - Prob. 15.29SPCh. 15 - Prob. 15.30SPCh. 15 - Prob. 15.31SPCh. 15 - Prob. 15.32SPCh. 15 - Prob. 15.33SPCh. 15 - Give the structures of the products represented by...Ch. 15 - Furan and malemide undergo a Diels-Alder reaction...Ch. 15 - Prob. 15.36SPCh. 15 - Prob. 15.37SPCh. 15 - Prob. 15.38SPCh. 15 - Prob. 15.39SPCh. 15 - Determine whether each structure is likely to be...Ch. 15 - An important variation of the Diels-Alder reaction...
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