Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 8, Problem 92P
How would the following substituents affect the rate of a Diels-Alder reaction?
- a. an electron-donating substituent in the diene
- b. an electron-donating substituent in the dienophile
- c. an electron-withdrawing substituent in the diene
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Draw the product formed when each diene and dienophile react in a Diels-Alder reaction.
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ion 18 of 20
Consider the Diels-Alder reaction shown. Draw the structures of the diene and dienophile that yield the enantiomeric products
in the Diels-Alder reaction and consider whether an endo or exo addition occurs.
product 1
product 2
... H
Diene
+
Dienophile
Draw the diene.
Draw the dienophile.
Erase
Select
Draw
Rings
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Erase
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Rings
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C
Chapter 8 Solutions
Organic Chemistry (8th Edition)
Ch. 8.1 - Prob. 1PCh. 8.1 - Prob. 2PCh. 8.4 - Prob. 3PCh. 8.5 - Prob. 4PCh. 8.5 - Prob. 6PCh. 8.6 - a. Predict the relative bond lengths of the three...Ch. 8.6 - Prob. 8PCh. 8.6 - Prob. 9PCh. 8.6 - Prob. 10PCh. 8.7 - Prob. 11P
Ch. 8.7 - Prob. 12PCh. 8.7 - Prob. 13PCh. 8.8 - Prob. 14PCh. 8.8 - Prob. 15PCh. 8.8 - Prob. 16PCh. 8.9 - Which member of each pair is the stronger acid?Ch. 8.9 - Which member of each pair is the stronger base? a....Ch. 8.9 - Rank the following compounds from strongest acid...Ch. 8.10 - Prob. 20PCh. 8.10 - Which acid in each of the following pairs is...Ch. 8.10 - Prob. 23PCh. 8.11 - Prob. 24PCh. 8.11 - Prob. 26PCh. 8.12 - Prob. 27PCh. 8.12 - Prob. 28PCh. 8.12 - Prob. 29PCh. 8.12 - Prob. 30PCh. 8.12 - Prob. 31PCh. 8.12 - Prob. 32PCh. 8.13 - Prob. 33PCh. 8.13 - Prob. 34PCh. 8.13 - Prob. 35PCh. 8.13 - What are the major 1,2- and 1,4-addition products...Ch. 8.13 - Prob. 38PCh. 8.14 - Prob. 39PCh. 8.14 - Prob. 40PCh. 8.14 - Prob. 41PCh. 8.14 - Prob. 42PCh. 8.14 - Prob. 43PCh. 8.14 - Prob. 44PCh. 8.14 - Prob. 46PCh. 8.15 - Prob. 47PCh. 8.17 - Prob. 48PCh. 8.17 - Prob. 49PCh. 8.18 - Prob. 50PCh. 8.18 - Prob. 52PCh. 8.18 - Prob. 53PCh. 8.18 - Prob. 54PCh. 8.19 - Prob. 55PCh. 8.20 - Prob. 56PCh. 8.20 - What orbitals contain the electrons represented as...Ch. 8.20 - Prob. 59PCh. 8.20 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - Prob. 65PCh. 8 - Prob. 66PCh. 8 - Prob. 67PCh. 8 - Prob. 68PCh. 8 - Prob. 69PCh. 8 - Prob. 70PCh. 8 - Prob. 71PCh. 8 - Prob. 72PCh. 8 - Prob. 73PCh. 8 - Which compound is the strongest base?Ch. 8 - Prob. 75PCh. 8 - Prob. 76PCh. 8 - a. The A ring (Section 3.16) of cortisone (a...Ch. 8 - Prob. 78PCh. 8 - Prob. 79PCh. 8 - Prob. 80PCh. 8 - Prob. 81PCh. 8 - Purine is a heterocyclic compound with four...Ch. 8 - Prob. 83PCh. 8 - Why is the delocalization energy of pyrrole (21...Ch. 8 - Prob. 85PCh. 8 - Prob. 86PCh. 8 - Prob. 87PCh. 8 - A student obtained two products from the reaction...Ch. 8 - Prob. 89PCh. 8 - a. How could each of the following compounds be...Ch. 8 - Draw the products obtained from the reaction of...Ch. 8 - How would the following substituents affect the...Ch. 8 - Prob. 93PCh. 8 - The acid dissociation constant (Ka) for loss of a...Ch. 8 - Protonated cyclohexylamine has a Ka = 1 1011...Ch. 8 - Draw the product or products that would be...Ch. 8 - Prob. 97PCh. 8 - Prob. 98PCh. 8 - Prob. 99PCh. 8 - Prob. 100PCh. 8 - Prob. 101PCh. 8 - a. Propose n mechanism for the following reaction:...Ch. 8 - Prob. 103PCh. 8 - As many as 18 different Diels-Alder products can...Ch. 8 - Prob. 105PCh. 8 - Prob. 106PCh. 8 - Prob. 107PCh. 8 - Prob. 108PCh. 8 - The experiment shown next and discussed in Section...Ch. 8 - Prob. 110PCh. 8 - Prob. 111PCh. 8 - Prob. 112PCh. 8 - Prob. 1PCh. 8 - Prob. 2PCh. 8 - Prob. 3PCh. 8 - Prob. 4PCh. 8 - Prob. 5PCh. 8 - Prob. 6PCh. 8 - Prob. 7PCh. 8 - Prob. 8PCh. 8 - Prob. 9PCh. 8 - Prob. 10PCh. 8 - Prob. 11PCh. 8 - Prob. 12P
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- Label each diene as reactive or unreactive in a Diels–Alder reaction.arrow_forwardWhat is the major organic product of the following Diels-Alder reaction? Me₂N. A. B. C. D. Me₂N Me₂N Me₂N OHC Me₂N CHO CHO CHO CHO 5 heatarrow_forwardDeconstruct the given Diels–Alder adduct. Draw the reactants (A and B), in any order, that would be needed to produce the Diels–Alder adduct.arrow_forward
- The diene shown below will NOT react in a Diels-Alder reaction. Why not? Select one: A. The compound is not a conjugated diene. B. The compound is lacking in electron withdrawing groups. O C. This compound cannot adopt the s-cis conformation. D. The compound is lacking in electron donating groups.arrow_forwardDraw the correct product for the given Diels-Alder reaction. Select Draw Rings Morearrow_forwardThank you!arrow_forward
- 7. At room temperature cyclopentadiene reacts with itself to form dicyclopentadiene in a Diels-Alder reaction. a) draw the self reaction of cyclopentadiene 20°C. b) When dicyclopentadiene is heated to boiling (170°C), the retor-Diels-Alder reaction occurs producing 2 moles of cyclopentadiene. Explain this observation in terms of free energy, enthalpy and entropy. c) If the AHxn = -75 kJ/mol and the ASpxn = -226 J/mol K, What temperature would be required for the reaction to be at equilibrium (Keq = 1).arrow_forwardProvide an explanation for why the stereoisomers shown below would not be produced in the Diels-Alder reaction..arrow_forwardA Moving to another question will save this response. Question 20 For a diene to undergo a Diels-Alder reaction it must: O A. be able to adopt cyclohexane O B. be substituted with electron-withdrawing groups. Oc. be able to adopt and s-trans conformation. O D. be able to adopt an s-cis conformation. O E. be substituted with electron-donating groups. Moving to another question will save this response. O Type here to searcharrow_forward
- 1. Draw the structure of the dimer of cyclopentadiene. 2. What is the IUPAC name of the product formed in this Diels-Alder reaction? 3. Explain why the endo product is preferred in this Diels-Alder reaction. Draw the reaction mechanism, if needed.arrow_forwardWhy a conjugated diene is more stable than an isolated diene ?arrow_forward10. The following compound was produced in a Diels-Alder reaction. COOH a) How many sp³ hybridized carbons are in this molecule? b) Is this molecule chiral? c) Are the carboxylic acid substituents electron donating group or electron withdrawing group? d) Draw the diene and dienophile which would react together to give this product.arrow_forward
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