Concept explainers
(a)
Interpretation:
The product that is obtained from the Diels-Alder reaction of
Concept introduction:
Diels-Alder reaction is a reaction between conjugated diene and
(b)
Interpretation:
The product that is obtained from the Diels-Alder reaction of
Concept introduction:
Diels-Alder reaction is a reaction between conjugated diene and alkene. It is also known as
(c)
Interpretation:
The condition that is required to favor the formation of the product in part (a) is to be stated.
Concept introduction:
Diels-Alder reaction is a reaction between conjugated diene and alkene. It is also known as
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EBK ORGANIC CHEMISTRY
- (3) HI does not undergo free radical addition with 1-butene, even in the presence of a peroxide. Please provide an explanation by analyzing the propagation steps if the same radical reaction occurred with HI. Besides the bond dissociation enthalpies in the appendix, the following approximate bond dissociate enthalpies might be useful to you: ~310 kJ/mol The component of C=C CH3CH₂CH₂CH₂-Br CH3CH₂CH₂CH2-I -290 kJ/mol (C-Br bond) ~235 kJ/mol (C-I bond)arrow_forwardThe diene lactone shown in part (a) has one electron-donating group (¬OR) and one electron-withdrawing group(C“O). This diene lactone is sufficiently electron-rich to serve as the diene in a Diels–Alder reaction.(a) What product would you expect to form when this diene reacts with methyl acetylenecarboxylate, a strong dienophile?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
- 2) Predict the major product for each Diels-Alder reaction. Include stereochemistry where appropriate. H. C=N (a) H H. CH3 CH;O, (b) Ph (c) Pharrow_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_forwardWhat are the expected kinetic and thermodynamic products from addition of one mole of Br, to the following dienes? (a) (Б)arrow_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 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.arrow_forward6) The Diels-Alder reaction of anthracene (which is achiral) and maleic anhydride (also achiral) results in the formation of an achiral product. This is not always the case (where two achiral reactants form an achiral product). a) Propose a Diels-Alder reaction where two achiral starting materials result in the formation of a chiral product. b) Would this chiral product be a single enantiomer or a racemic mixture?arrow_forward4B1 Write the possible reactants that gave the following products in the Diels-Alder reaction osoarrow_forward
- Step 6: Now that you have determined the substrates and mechanism of a Diels-Alder reaction, you will learn how to recognize when you should use the Diels-Alder reaction. In a synthesis reaction, if you are given a cyclohexene product with no other obvious functional group transformations and an electron-withdrawing group two carbons away from the alkene, it is likely made via the Diels-Alder reaction. Deduce the structures of the starting materials to form the Diels-Alder adduct shown. ..... CN CN Diene + Dienophilearrow_forward(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?(c) Draw resonance forms to show the charge distribution on the pyrrole structure.arrow_forward6) Provide the enantiomeric Diels-Alder adducts that would form from the following reaction along with the two transition states leading to them: + HO₂Carrow_forward
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