It is to be explained if diene A or diene B 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 24.7P

Interpretation Introduction

Interpretation:

It is to be explained if diene A or diene B 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

(a 4 shows scanning electron microscope (SEM) images of extruded actions of packing bed for two capillary columns of different diameters, al 750 (bottom image) and b) 30-μm-i.d. Both columns are packed with the same stationary phase, spherical particles with 1-um diameter. A) When the columns were prepared, the figure shows that the column with the larger diameter has more packing irregularities. Explain this observation. B) Predict what affect this should have on band broadening and discuss your prediction using the van Deemter terms. C) Does this figure support your explanations in application question 33? Explain why or why not and make any changes in your answers in light of this figure. Figure 4 SEM images of sections of packed columns for a) 750 and b) 30-um-i.d. capillary columns.³

fcrip = ↓ bandwidth Il temp 32. What impact (increase, decrease, or no change) does each of the following conditions have on the individual components of the van Deemter equation and consequently, band broadening? Increase temperature Longer column Using a gas mobile phase instead of liquid Smaller particle stationary phase Multiple Paths Diffusion Mass Transfer

34. Figure 3 shows Van Deemter plots for a solute molecule using different column inner diameters (i.d.). A) Predict whether decreasing the column inner diameters increase or decrease bandwidth. B) Predict which van Deemter equation coefficient (A, B, or C) has the greatest effect on increasing or decreasing bandwidth as a function of i.d. and justify your answer. Figure 3 Van Deemter plots for hydroquinone using different column inner diameters (i.d. in μm). The data was obtained from liquid chromatography experiments using fused-silica capillary columns packed with 1.0-μm particles. 35 20 H(um) 큰 20 15 90 0+ 1500 100 75 550 01 02 594 05 μ(cm/sec) 30 15 10