The first step in a synthesis of dodecahedrane involves a Diels-Alder reaction betweenthe cyclopentadiene derivative (1) and dimethyl acetylenedicarboxylate (2). Show howthese two molecules react to form the dodecahedrane synthetic intermediate (3).+ CH,0OCC=CCOOCH,COOCHČOOCH3Cyclopentadienyl-cyclopentadiene(1)Dimethyl acetylene-dicarboxylate(2)(3)

Dimethyl acetylenedicarboxylate firstly reacts with one of the diene present in cyclopentadienyl…

Answered: The first step in a synthesis of…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

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Problem 62AP

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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 °C
Uemura and coworkers studied a time dependent Diels-Alder reaction which first formed the endo product as the major organic product and with time produced the exo product (J. Org. Chem. 2018, 83, 9300−9304). Show the endo and exo product for the reaction below. Which is the thermodynamic product and which is the kinetic product? Explain your reasoning.
Chemistry Give the products of the reaction of 1 mole of 2-methy1-1,3-pentadiene with 1 mole of HBr. Whichproduct(s) will predominate if the reaction is under kinetic control? Which products) will predominateif the reaction is under thermodynamic control?
Show that the [6 + 2] cyclization of hexa-1,3,5-triene with maleic anhydride is thermally forbidden but photochemicallyallowed.(e) Show the Diels–Alder product that would actually result from heating hexa-1,3,5-triene with maleic anhydride.
Give major products for 1,2-/1,4-additions (A) Diels-Alder (B-D) cycloadditions [2+2] cycloadditions , and Retro-Diels-Alder (E) cycloaddition. Illustrate the regiochemistry and stereochemistry (me so, enatiomer., exo or Endo) for cycloadditions B-D?
When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 °C, an interesting Diels–Alderadduct of formula C20H14 results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and abroad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings ofanthracene reacted as a diene
A solution of 5-methylcyclopenta-1,3-diene rearranges at roomtemperature to a mixture containing 1-methyl-, 2-methyl-, and 5-methylcyclopenta-1,3-diene. (a) Show how both isomeric products areformed from the starting material by a sigmatropic rearrangementinvolving a C–H bond. (b) Explain why 2-methylcyclopenta-1,3-diene isnot formed directly from 5-methylcyclopenta-1,3-diene by a [1,3]rearrangement.
Predict the product and then show mechanism. (Diels-alder reaction)
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 oftenpredominates. Draw the resonance hybrid for each reactant, and use thecharge distribution of the hybrids to explain why the 1,2-disubstitutedproduct is the major product.
Explain [3,3] Sigmatropic Rearrangements ?
The bicyclic alkene P can be prepared by thermal electrocyclic ringclosure from cyclodecadiene Q or by photochemical electrocyclic ringclosure from cyclodecadiene R. Draw the structures of Q and R, andindicate the stereochemistry of the process by which each reactionoccurs.
Define about Sigmatropic Rearrangements ?

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