Interpretation:
In the given Diels-Alder reaction, the C atoms in the product that have rehybridized from
Concept introduction:
The [
Want to see the full answer?
Check out a sample textbook solutionChapter 24 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- 7. Predict the product of the Diels-Alder reaction of this compound with 1,3-cyclohexadiene (not shown). You do not have to consider stereochemistry. Bicyclic templates are shown to the right.arrow_forwardExp3: 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_forwardConsider the following dienes in a Diels–Alder reaction with ethene. Which will react the fastest? Which will react the slowest? Explainarrow_forward
- Diels–Alder reaction of a monosubstituted diene (such as CH2=CH– CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant, and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.arrow_forwardGive the molecule that undergoes an intramolecular Diels- Alder cycloaddition to produce the given cycloadduct product.racemic H .OCH 3 racemicarrow_forwardWhich of the following compounds can arise directly from a Diels-Alder reaction? Circle any structures that can. Then, identify the appropriate diene(s) and dienophile(s) that would lead to the compound. Pay attention to E-/Z- stereochemistry in all of the reactants. For those that cannot undergo a Diels-Alder reaction, please explain why.arrow_forward
- The A ring of cortisone (a steroid) is formed by a Diels–Alder reaction using the two reactants shown here. What is the product of this reaction?arrow_forwardShow the product of the Diels–Alder dimerization of cyclobutadiene. (This reaction is similar to the dimerization of cyclopentadiene)arrow_forwardDiels—Alder reaction of a monosubstituted diene (such as CH2 = CH – CH = CHOCH3) with a monosubstituted dienophile (such as CH2 = CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.arrow_forward
- Draw the structures of the diene and dienophile that yield the following enantiomeric products in the Diels-Alder reaction below: Diene: Dienophile: Do the products represent an endo or an exo addition of dienophile to diene? left product is endo, right product is exo left product is exo, right product is endo both products are endo both products are exoarrow_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_forward1. Consider the Diels-Alder cycloaddition reaction below. D heat H D = deuterium = 2H Draw the major regioisomer (or in other words, constitutional isomer) expected to form. Draw appropriate resonance structures and explain why only one constitutional isomer is expected to form. Discuss if this can be drawn with both groups on the dieneophile being endo or one has to be endo and the other has to be exo.arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY