VII. For each of the following Diels-Alder reactions, provide the structure of the missing reagent(s) or product. To receive full credit, be sure to include stereochemistry when appropriate. CH3 NC ° OCH3 CI H3C CO₂Me H3C CO₂Me H H3C H CH3 H

VII. For each of the following Diels-Alder reactions, provide the structure of the missing reagent(s) or product. To receive full credit, be sure to include stereochemistry when appropriate. CH3 NC ° OCH3 CI H3C CO₂Me H3C CO₂Me H H3C H CH3 H

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.35P: The following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product....

See similar textbooks

Question

VII. For each of the following Diels-Alder reactions, provide the structure of the missing
reagent(s) or product. To receive full credit, be sure to include stereochemistry when appropriate.
CH3
NC
°
OCH3
CI
H3C
CO₂Me
H3C
CO₂Me
H
H3C
H
CH3
H

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

SEE SOLUTION Check out a sample Q&A here

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Similar questions

Predict the product of the following Diels-Alder reactions, using the correct stereo- and regiochemistry. Make sure you include a detailed explanation of your answer, and provide arrows for mechanisms of needed.
One of the following Diels-Alder reactions will occur more rapidly than the other. Draw the major, organic product for only the faster of these two reactions. You do not need to account for stereochemistry, but be sure your answer accounts for regiochemistry, where appropriate. CH3 H,C HN H,C ČH, N. H CH3 H2C ČH,
Compounds P and Q can undergo a Diels-Alder reaction to form two regioisomeric products R and S as shown in Figure 5. OMe O C8H12O2 R C8H12O2 S Figure 5 Draw the chemical structures of regioisomeric compounds R and S. Using possible resonance contributors of P and Q predict which of the two regioisomers will be favoured in the reaction. Using curly arrows, draw the mechanism for the reaction of P and Q to form the dominant regioisomer you have predicted in your answer to part (ii) above.
[Review Topics] [References] Draw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown. Diene + Dienophile CH3O CH₂ I wwwwwww
A) Write the mechanism and predict the products for the following reaction. Label each product as the thermodynamic product or the kinetic product. Write a few sentences explaining which product would predominate at low temperature and which would predominate at high temperature and explain the reason for this result. HBr ABd B) Choose reagents that would give the following product in a Diels-Alder reaction: C) Predict the major and minor product for the following Diels-Alder reaction:
Which of the following compounds can arise directly from a Diels-Alder reaction? Circle any structures that can. Then, identify the appropriate diene(s) and dienophile(s) that would lead to the compound. Pay attention to E-/Z- stereochemistry in all of the reactants. For those that cannot undergo a Diels-Alder reaction, please explain why.
(a) Complete the following sequence of reactions (i.e., give the structure for compounds A and B), giving structural details of all key intermediates. heat & A COOCH3 H₁₂ Ni (b) Provide the bond line structures for the pair of compounds used for the Diels-Alder synthesis of the compound shown below. O B COOCH3 (c) Draw the two major products obtained when (3E,5Z)-2,2,3,6,7-pentamethylocta-3,5-diene reacts with HBr at low and high temperatures. Label the products as the kinetic or thermodynamic product AND, if applicable, use dashes and wedges to show the correct stereochemistry in the obtained products.
Following is an example of a type of reaction known as a Diels-Alder reaction 1,3-Pentadiene Ethylene 3-Methylcyclohexene (a racemic mixture) The Diels-Alder reaction between a diene and an alkene is quite remarkable in that it is one of the few ways that chemists have to form two new carbon-carbon bonds in a single reaction. Given what you know about the relative strengths of carbon-carbon sigma and pi bonds, would you predict the Diels-Alder reaction to be exothermic or endothermic? Explain your reasoning.
The following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product. Account for the observation that the Diels-Alder reaction given in this problem takes place under milder conditions (at lower temperature) than the analogous Diels-Alder reaction shown in Problem 20.34.
3. The following reactions are not technically the Diels-Alder reaction, but you should still be able to predict the product (with appropriate regio/stereochemistry). (a) (b) OMe OMe H3C N + NC H3C. CN CH3
Which of the following compounds can arise directly from a Diels-Alder reaction? Please circle any structures that can, and then identify the appropriate diene(s) and dienophile(s) that would lead to that compound. Be sure to pay attention to E-IZ- stereochemistry in all of the reactants. For those that cannot undergo a Diels-Alder reaction, please explain why. OEt o CN .cO,Me Meo OMe H (+-) (+/-) (+/-) (+/-)
Identify the expected major product of the following Diels-Alder reaction. (Showmechanism and stereochemistry) please mention proper stereochemistry,