EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 8, Problem 77P
a. The A ring (Section 3.16) of cortisone (a steroid) is formed by a Diels—Alder reaction using the two reactants shown here. What is the product of this reaction?
b. The C ring of estrone (a steroid) is formed by a Diels-Alder reaction using the two reactants shown here. What is the product of this reaction?
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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.
Compounds P and Q can undergo a Diels-Alder reaction to form two
regioisomeric products R and S as shown in Figure 5.
OMe
O
C8H12O2
R
C8H12O2
S
Figure 5
Draw the chemical structures of regioisomeric compounds R and S.
Using possible resonance contributors of P and Q predict which of the two
regioisomers will be favoured in the reaction.
Using curly arrows, draw the mechanism for the reaction of P and Q to form the
dominant regioisomer you have predicted in your answer to part (ii) above.
4
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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Exp3: Diels-Alder reaction Why does cyclopentadiene regularly form a dimer? How to break the dimer into monomers? Does the diene in this reaction act as the nucleophile or the electrophile? Is the maleic anhydride a nucleophile or an electrophile in this reaction? Explain your reasoning.arrow_forward3. Consider the following Diels-Alder reaction: a) Draw a detailed mechanism for the reaction and show the structures of the endo and exo products. b) Label the endo and exo product in part a. c) Which transition state is lower in energy, the one leading to the exo product or the one leading to the endo product? d) Which product do you expect to be more stable (the exo or the endo product) and why?arrow_forwardThe diene shown below will NOT react in a Diels-Alder reaction. Why not? Select one: DA. The compound is not a conjugated diene. OB. This compound cannot adopt the s-cis conformation. C. The compound is lacking in electron donating groups. ⒸD. The compound is lacking in electron withdrawing groups.arrow_forward
- (A) Which triene has the smallest heat of hydrogenation? Explain why. (B) Which triene can be reactive in the Diels-Alder reaction? (C) Which triene is the most reactive in the Diels-Alder reaction?arrow_forwardZingiberene and β-sesquiphellandrene, natural products obtained from ginger root, contain conjugated diene units. Which diene reacts faster in the Diels–Alder reaction and why?arrow_forward16.7 Diels-Alder Reactions Predict the major product of the following reaction. + heat ?arrow_forward
- A benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.arrow_forwardWhy does Hammett Equation only apply to meta and para substituted rings and not others? Explainarrow_forwardDraw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown. Diene + Dienophile ? CH3 Consider E/Z stereochemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu. Lits O. Sn [F CH3arrow_forward
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