Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 8, Problem 89P
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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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?
Draw the correct product for the Diels-Alder reaction.
Select
/
Draw
C
Rings
H
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Chapter 8 Solutions
Organic Chemistry
Ch. 8.1 - Prob. 1PCh. 8.1 - Prob. 2PCh. 8.4 - Prob. 3PCh. 8.5 - Prob. 5PCh. 8.6 - a. Predict the relative bond lengths of the three...Ch. 8.6 - Prob. 7PCh. 8.6 - Prob. 8PCh. 8.8 - Prob. 9PCh. 8.9 - Prob. 10PCh. 8.9 - Prob. 12P
Ch. 8.9 - Prob. 13PCh. 8.10 - Prob. 14PCh. 8.10 - What orbitals contain the electrons represented as...Ch. 8.10 - Prob. 16PCh. 8.10 - Prob. 17PCh. 8.11 - Prob. 18PCh. 8.11 - Prob. 19PCh. 8.11 - Prob. 20PCh. 8.12 - Prob. 21PCh. 8.12 - Prob. 22PCh. 8.12 - Prob. 23PCh. 8.13 - Prob. 24PCh. 8.13 - Prob. 25PCh. 8.13 - Prob. 26PCh. 8.14 - Prob. 27PCh. 8.14 - Prob. 28PCh. 8.14 - Prob. 29PCh. 8.15 - Which member of each pair is the stronger acid?Ch. 8.15 - Which member of each pair is the stronger base? a....Ch. 8.15 - Rank the following compounds from strongest acid...Ch. 8.15 - Prob. 34PCh. 8.16 - Prob. 35PCh. 8.17 - Prob. 37PCh. 8.17 - Prob. 38PCh. 8.17 - Prob. 39PCh. 8.17 - Prob. 40PCh. 8.17 - Prob. 41PCh. 8.17 - Prob. 42PCh. 8.18 - Prob. 43PCh. 8.18 - Prob. 44PCh. 8.18 - Prob. 45PCh. 8.18 - Prob. 47PCh. 8.19 - Prob. 48PCh. 8.19 - Prob. 49PCh. 8.19 - Prob. 50PCh. 8.19 - Prob. 51PCh. 8.19 - Prob. 52PCh. 8.19 - Prob. 53PCh. 8.19 - Prob. 55PCh. 8.20 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Prob. 58PCh. 8 - Prob. 59PCh. 8 - 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 - Which compound is the strongest base?Ch. 8 - Prob. 71PCh. 8 - Prob. 72PCh. 8 - Prob. 73PCh. 8 - Prob. 74PCh. 8 - Prob. 75PCh. 8 - Prob. 76PCh. 8 - Prob. 77PCh. 8 - Prob. 78PCh. 8 - Purine is a heterocyclic compound with four...Ch. 8 - Prob. 80PCh. 8 - Why is the delocalization energy of pyrrole (21...Ch. 8 - Prob. 82PCh. 8 - Prob. 83PCh. 8 - Prob. 84PCh. 8 - A student obtained two products from the reaction...Ch. 8 - Prob. 86PCh. 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. 90PCh. 8 - The acid dissociation constant (Ka) for loss of a...Ch. 8 - Protonated cyclohexylamine has a Ka = 1 1011...Ch. 8 - Prob. 93PCh. 8 - Prob. 94PCh. 8 - Prob. 95PCh. 8 - Prob. 96PCh. 8 - Prob. 97PCh. 8 - a. Propose n mechanism for the following reaction:...Ch. 8 - Prob. 99PCh. 8 - As many as 18 different Diels-Alder products can...Ch. 8 - Prob. 101PCh. 8 - Prob. 102PCh. 8 - Prob. 103PCh. 8 - Prob. 104PCh. 8 - The experiment shown next and discussed in Section...Ch. 8 - Prob. 106PCh. 8 - Prob. 107PCh. 8 - Prob. 108PCh. 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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- 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 More Erase Select Draw Rings More Carrow_forwardDraw the correct product for the Diels-Alder reaction. Select Carrow_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
- Draw 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_forward8. Which factors affect the reaction rate in Diels-Alder reactions? O A. Electron donating group on the diene and electron withdrawing group on dienophile. O B. Electron donating group on both the diene and the dienophile. OC. Electron withdrawing group on both the diene and the dienophile. OD. Addition of catalyst.arrow_forwardLabel each diene as reactive or unreactive in a Diels–Alder reactionarrow_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_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_forwardD. Provide a reasonable mechanism for the Diels-Alder reaction between two molecules of cyclopenta-1,3-diene. Br 1. Mg 2.CO₂ 3. H₂O* OHarrow_forward
- Draw the correct product for the Diels-Alder reaction.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_forwarda.How many π electrons does C contain? b.How many π electrons are delocalized in the ring? c.Explain why C is aromatic.arrow_forward
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