Concept explainers
(a)
Interpretation:
Effect of electron donating substituents in the diene of Diels-Alder reactions has to be predicted.
Concept Introduction:
Diels-Alder reaction:
A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.
(b)
Interpretation:
The effect of electron donating substituents in dienophile of Diels-Alder reactions has to be predicted.
Concept Introduction:
Diels-Alder reaction:
A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.
(c)
Interpretation:
The effect of electron withdrawing substituents in diene of Diels-Alder reactions has to be predicted.
Concept Introduction:
Diels-Alder reaction:
A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.
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Essential Organic Chemistry, Global Edition
- The Diels–Alder reaction, a powerful reaction discussed in Chapter 14, occurs when a 1,3-diene such as A reacts with an alkene such as B to form the six-membered ring in C. a.Draw curved arrows to show how A and B react to form C. b.What bonds are broken and formed in this reaction? c.Would you expect this reaction to be endothermic or exothermic? d.Does entropy favor the reactants or products? e. Is the Diels–Alder reaction a substitution, elimination, or addition?arrow_forward8. Which factors affect the reaction rate in Diels-Alder reactions? O A. Electron donating group on the diene and electron withdrawing group on dienophile. O B. Electron donating group on both the diene and the dienophile. OC. Electron withdrawing group on both the diene and the dienophile. OD. Addition of catalyst.arrow_forwardDraw the correct product for the Diels-Alder reaction. Select Carrow_forward
- Draw out both reactants and the Diels-Alder products from reaction of the following: a. furan and trans-2-butene b. 1,3-cyclohexadiene and 2-butyne c. 1,3-butadiene and cis-2-pentenearrow_forwardWhat is the major organic product of the following Diels-Alder reaction? Me₂N. A. B. C. D. Me₂N Me₂N Me₂N OHC Me₂N CHO CHO CHO CHO 5 heatarrow_forwardLabel each diene as reactive or unreactive in a Diels–Alder reactionarrow_forward
- 7. At room temperature cyclopentadiene reacts with itself to form dicyclopentadiene in a Diels-Alder reaction. a) draw the self reaction of cyclopentadiene 20°C. b) When dicyclopentadiene is heated to boiling (170°C), the retor-Diels-Alder reaction occurs producing 2 moles of cyclopentadiene. Explain this observation in terms of free energy, enthalpy and entropy. c) If the AHxn = -75 kJ/mol and the ASpxn = -226 J/mol K, What temperature would be required for the reaction to be at equilibrium (Keq = 1).arrow_forwardConsider the four trienes E–H.a.Rank compounds E–H in order of increasing heat of hydrogenation. b.Which compound is most reactive in the Diels–Alder reaction? c. Which compound(s) are unreactive in the Diels–Alder reaction? d.Which compound absorbs the longest wavelength of ultraviolet light?arrow_forwardDraw the correct product for the Diels-Alder reaction.arrow_forward
- D. Provide a reasonable mechanism for the Diels-Alder reaction between two molecules of cyclopenta-1,3-diene. Br 1. Mg 2.CO₂ 3. H₂O* OHarrow_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_forwarda.How many π electrons does C contain? b.How many π electrons are delocalized in the ring? c.Explain why C is aromatic.arrow_forward
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