7. Diels-Alder reactions are not limited to dienes and dienophiles with only carbon atoms like we have seen in lecture. Other atoms (heteroatoms) can be included in the system of the diene and/or the dienophile. The following are examples of hetero Diels-Alder reactions. Draw the mechanism and predict the product of both reactions, paying particular attention to stereochemistry. H O MeO₂C + CO₂Me +

7. Diels-Alder reactions are not limited to dienes and dienophiles with only carbon atoms like we have seen in lecture. Other atoms (heteroatoms) can be included in the system of the diene and/or the dienophile. The following are examples of hetero Diels-Alder reactions. Draw the mechanism and predict the product of both reactions, paying particular attention to stereochemistry. H O MeO₂C + CO₂Me +

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 20.33P

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True or False: Acetylene is a naturally occurring conjugated diene True or False: The Diels-Alder reaction has the stereochemistry of the dienophile is retained in the product. True or False: When looking at kinetic vs. thermodynamic products the kinetic product predominates at low temperature. True or False: the mechanism of the Diels-Alder reaction is three π bonds break; one σ bond and two π bonds form.
Please ex plain and Please show all arrow pushing mechaarsas. Thank you!
A2 What is the inverse electron demand Diels–Alder reaction? Please pick a pair of a diene and a dienophile from the following dienes and dienophile that will undergo this type of reaction. Please show how this reaction works using Frontier Molecular Orbitals. What is the reaction product?
4.- Predict the product for each Diels-Alder reaction. Indicate stereochemistry where appropriate. स a) b) H3C, H3C + H3C CHO A ent 10 150 COOH + ·E· <- c) COOH BAS 5.- Retro Diels-Alder: show a combination of diene and dienophile that would result in each Diels-Alder adduct.
6) 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?
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:
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.
b) Which of these dienophiles gives the FASTEST reaction with cyclopentadiene? CH2 CH2 A. | В. C. | D. | Give structures for the major Diels-Alder product of the following reactions: 1,3- cyclohexadiene and tetrachloroethene 1,3-cylcohexadiene and fumaric acid, the trans isomer of maleic acid с.
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.
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) Ph
to doinw 4. -> A) Which of the following is NOT a suitable diene for a Diels-Alder reaction? ultiple alkylation B) HBr CHEM 242 Activity 2.1-Conjugated-Systems D) 5. In the addition of HBr to 1,3-butadiene, one product is called the kinetic product and the other is called the thermodynamic product. doccriptors that apply to the kinetic product.
Exp3: Diels-Alder reaction Why does cyclopentadiene regularly form a dimer? How to break the dimer into monomers? Does the diene in this reaction act as the nucleophile or the electrophile? Is the maleic anhydride a nucleophile or an electrophile in this reaction? Explain your reasoning.