Interpretation:
The given conformations are to be classified as s-cis and s-trans. The one which can undergo a Diels-Alder reaction is also to be identified.
Concept introduction:
The Diels-Alder reaction is single step concerted reaction. The concerted nature of the Diels-Alder reaction means that both of the new carbon-carbon
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Organic Chemistry: Principles and Mechanisms (Second Edition)
- Which of the following dienes have an s-cis conformation, and which have an s-trans conformation? Of the s-trans dienes, which can readily rotate to s-cis?arrow_forwardWhich of the structures below is the major product obtained from the following Diels-Alder reaction. Note that you will have to re-draw the diene in the s-cis conformation to correctly predict the stereochemistry of the product. ? A B Carrow_forwardExpain the below Rule: The diene can react only when it adopts the s-cis conformation.arrow_forward
- The first alkene which requires the position of the double bond to be indicated is?arrow_forwardChoose the correct option. 1. Which of the following reactions best describes the Diels-Alder reaction?A)electrocyclic reactionB)cycloaddition reactionC)sigmatropic reactionD)radical reactionE)nucleophilic substitution reaction 2.Which of the following statements best describes the theory of Conservation of Orbital Symmetry?A)Molecular orbital of the transition state must be similar to that of the reactant.B)Molecular orbital of the transition state must be similar to that of the product.C)Only s orbitals from reactants and products are utilized.D)Molecular orbitals of reactant and product must have similar symmetry.E)Molecular orbitals of reactant and product must have different symmetry. 3.Through what type of single pericyclic reaction did the reaction proceed? 5-methylcyclopenta-1,3-diene to 1-methylcyclopenta-1,3-dieneA)[1,2] sigmatropic hydrogen migrationB)[1,3] sigmatropic hydrogen migrationC)[1,4] sigmatropic hydrogen migrationD)[1,5] sigmatropic hydrogen migrationE)none of the…arrow_forwardIf the elimination reaction can result in the formation of two different alkenes which one with predominate in the product?arrow_forward
- Furan and maleimide undergo a Diels–Alder reaction at 25 °C to give the endo isomer of the product. When the reactiontakes place at 90 °C, however, the major product is the exo isomer. Further study shows that the endo isomer of theproduct isomerizes to the exo isomer at 90 °C.furan: O maleimide:OON H(a) Draw and label the endo and exo isomers of the Diels–Alder adduct of furan and maleimide.(b) Which isomer of the product would you usually expect from this reaction? Explain why this isomer is usually favored.(c) Examine your answer to (b) and determine whether this answer applies to a reaction that is kinetically controlled orone that is thermodynamically controlled, or both.(d) Explain why the endo isomer predominates when the reaction takes place at 25 °C and why the exo isomer predominates at 90 °Carrow_forwardDraw the structure of each of the following molecules. (a) (R)-3-chloropent-1-ene; (b) (2S,3S)-2-bromo-3-chloropentane; (c) (R)-1-bromo-(R)-2-iodocyclopentane; (d) (S)-3-chlorocyclohexene; (e) (1R,2S)-1,2-dibromocyclopentanearrow_forwardDraw the structure for each of the following molecules. (a) 1,3-divinylcyclohexane; (b) 3-allyl-4-vinylcyclopentene;(c) dimethylacetylene; (d) divinyl ether; (e) 4-vinylocta-1,3,7-triene; (f) 2-allylcyclohexa-1,3-dienearrow_forward
- What is the product E and how is it formed? Can this be explained using frontier molecular orbital analysis? What would the regiochemistry and stereochemistry be?arrow_forwardEach of the following line structures can be described as a bicyclononane except for.arrow_forwardThe below reaction is a retro Diels-Alder reactions. Is is the reverse process of a Diels-Alder reaction with the formation of a diene and dienophile from some cyclohexene. It can be accomplished spontaneously with heat. Determine the product of the reaction. 4 Heatarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning