It is to be explained whether dienophile C or dienophile D will react faster in a standard Diels-Alder reaction. Concept introduction: [ 4+2 ] cycloaddition reactions are generally known as Diels-Alder reactions. A Diels-Alder reaction involves a diene and a dienophile. A diene shares four π electrons from the two conjugated π bonds while a dienophile shares two π electrons from a single π bond. The Diels-Alder reaction is concerted and proceeds through a six-membered aromatic transition state. For a Diels-Alder reaction to occur, the diene must be present in the s-cis conformation because both ends of the diene must be relatively close to the dienophile in the transition state. In a Diels-Alder reaction, the dienophile must be electron-poor, and the diene must be electron-rich. The electron-donating substituents bonded directly to the dienes carbons increase the rate of a Diels-Alder reaction. These are the same substituents as activating groups in electrophilic aromatic substitution. While electron-withdrawing substituents bonded directly to the dienophile carbons facilitate standard Diels-Alder reaction, these are the same substituents that act as deactivating groups in electrophilic aromatic substitution.

Question

Want to see the full answer?

Answer 1

Question

Chapter 24, Problem 24.8P

Interpretation Introduction

Interpretation:

It is to be explained whether dienophile C or dienophile D will react faster in a standard Diels-Alder reaction.

Concept introduction:

[4+2] cycloaddition reactions are generally known as Diels-Alder reactions. A Diels-Alder reaction involves a diene and a dienophile. A diene shares four π electrons from the two conjugated π bonds while a dienophile shares two π electrons from a single π bond. The Diels-Alder reaction is concerted and proceeds through a six-membered aromatic transition state. For a Diels-Alder reaction to occur, the diene must be present in the s-cis conformation because both ends of the diene must be relatively close to the dienophile in the transition state. In a Diels-Alder reaction, the dienophile must be electron-poor, and the diene must be electron-rich. The electron-donating substituents bonded directly to the dienes carbons increase the rate of a Diels-Alder reaction. These are the same substituents as activating groups in electrophilic aromatic substitution. While electron-withdrawing substituents bonded directly to the dienophile carbons facilitate standard Diels-Alder reaction, these are the same substituents that act as deactivating groups in electrophilic aromatic substitution.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Concentration Trial1 Concentration of iodide solution (mA) 255.8 Concentration of thiosulfate solution (mM) 47.0 Concentration of hydrogen peroxide solution (mM) 110.1 Temperature of iodide solution ('C) 25.0 Volume of iodide solution (1) used (mL) 10.0 Volume of thiosulfate solution (5:03) used (mL) Volume of DI water used (mL) Volume of hydrogen peroxide solution (H₂O₂) used (mL) 1.0 2.5 7.5 Time (s) 16.9 Dark blue Observations Initial concentration of iodide in reaction (mA) Initial concentration of thiosulfate in reaction (mA) Initial concentration of hydrogen peroxide in reaction (mA) Initial Rate (mA's)

Draw the condensed or line-angle structure for an alkene with the formula C5H10. Note: Avoid selecting cis-/trans- isomers in this exercise. Draw two additional condensed or line-angle structures for alkenes with the formula C5H10. Record the name of the isomers in Data Table 1. Repeat steps for 2 cyclic isomers of C5H10

Explain why the following names of the structures are incorrect. CH2CH3 CH3-C=CH-CH2-CH3 a. 2-ethyl-2-pentene CH3 | CH3-CH-CH2-CH=CH2 b. 2-methyl-4-pentene