EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: 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.
соон
CH3
a.
b.
C.
čoOCH3
The Diels–Alder reaction, a powerful reaction discussed in Chapter 14, occurs when a 1,3-diene such as A reacts with an alkene such as B to form the six-membered ring in C.
a.Draw curved arrows to show how A and B react to form C.
b.What bonds are broken and formed in this reaction?
c.Would you expect this reaction to be endothermic or exothermic?
d.Does entropy favor the reactants or products?
e. Is the Diels–Alder reaction a substitution, elimination, or addition?
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
EBK ORGANIC CHEMISTRY
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_forwardDraw out both reactants and the Diels-Alder products from reaction of the following: a. furan and trans-2-butene b. 1,3-cyclohexadiene and 2-butyne c. 1,3-butadiene and cis-2-pentenearrow_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_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_forwardDraw the product formed when each diene ½ dienophile react in a Diels- Alder reaction. 9. ходом C. +arrow_forward1. 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_forward
- 10. 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_forwardConsider the four trienes E–H.a.Rank compounds E–H in order of increasing heat of hydrogenation. b.Which compound is most reactive in the Diels–Alder reaction? c. Which compound(s) are unreactive in the Diels–Alder reaction? d.Which compound absorbs the longest wavelength of ultraviolet light?arrow_forward23.) A graduate student wanted to make the Diels. Alder Product A from the diene and dienophi se below. Draw the desired product A and now the mechanism for the reaction. 2 diene Aarrow_forward
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