Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 15.11A, Problem 15.16P
(a)
Interpretation Introduction
Interpretation:
The major product for the given Diels-Alder reaction is to be predicted.
Concept introduction:
Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene derivative. The dienophile adds to one side of the diene, and the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.
(b)
Interpretation Introduction
Interpretation:
The major product for the given Diels-Alder reaction is to be predicted.
Concept introduction:
Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.
(c)
Interpretation Introduction
Interpretation:
The major product for the given Diels-Alder reaction is to be predicted.
Concept introduction:
Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
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.
Provide products/reactants/reagents
stereochemistry and regiochemistry in mind.
for each Diels-Alder reaction below. Keep
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.
Chapter 15 Solutions
Organic Chemistry (9th Edition)
Ch. 15.2 - Prob. 15.1PCh. 15.2 - Prob. 15.2PCh. 15.2 - Prob. 15.3PCh. 15.4 - Prob. 15.4PCh. 15.4 - Prob. 15.5PCh. 15.5 - Treatment of an alkyl halide with AgNO3 in alcohol...Ch. 15.5 - Propose a mechanism for each reaction, showing...Ch. 15.6 - When Br2 is added to buta-1,3-diene at 15 C, the...Ch. 15.7 - Prob. 15.9PCh. 15.7 - When N-bromosuccinimide is added to hex-1-ene in...
Ch. 15.7 - Prob. 15.11PCh. 15.9 - Addition of 1-bromobut-2-ene to magnesium metal in...Ch. 15.10 - Show how you might synthesize the following...Ch. 15.11 - Predict the products of the following proposed...Ch. 15.11 - Prob. 15.15PCh. 15.11A - Prob. 15.16PCh. 15.11B - Prob. 15.17PCh. 15.11B - Predict the products of the following Diels-Alder...Ch. 15.12C - Prob. 15.19PCh. 15.12C - Prob. 15.20PCh. 15.13C - Prob. 15.21PCh. 15.13D - Using the examples in Table15-2 to guide you,...Ch. 15.14 - Phenolphthalein is an acid-base indicator that is...Ch. 15 - Prob. 15.24SPCh. 15 - Prob. 15.25SPCh. 15 - Show how the reaction of an allylic halide with a...Ch. 15 - Prob. 15.27SPCh. 15 - A solution was prepared using 0.0010 g of an...Ch. 15 - Prob. 15.29SPCh. 15 - Prob. 15.30SPCh. 15 - Prob. 15.31SPCh. 15 - Prob. 15.32SPCh. 15 - Prob. 15.33SPCh. 15 - Give the structures of the products represented by...Ch. 15 - Furan and malemide undergo a Diels-Alder reaction...Ch. 15 - Prob. 15.36SPCh. 15 - Prob. 15.37SPCh. 15 - Prob. 15.38SPCh. 15 - Prob. 15.39SPCh. 15 - Determine whether each structure is likely to be...Ch. 15 - An important variation of the Diels-Alder reaction...
Knowledge Booster
Similar questions
- 8) Predict the two products that form in following Diels-Alder reaction Circle the major product. CH₂O CH₂OCH, H O₂Narrow_forward[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 wwwwwwwarrow_forwardOf the three 1,4-diphenyl-1,3-butadiene isomers (E,E or E,Z or Z,Z) indicate the most suitable diene that can be used as a reactant in a Diels-Alder reaction. Explain your choice.arrow_forward
- For the Diels-Alder reaction, the product's skeletal structure and configuration at the bridgehead carbons are given (and the given wedge bond and dash bond should not be changed). Complete the structure of the major product. Indicate the stereochemistry, by adding two wedge and two dash bonds, at only the fused-ring stereocenters. A Complete the product and clearly show stereochemistry. H Harrow_forwardThis is a Diels-Alder reaction between ethylene and cis-1,3-butadiene. For each cycloaddition product, draw in all hydrogen atoms, and write the molecular formula below.arrow_forwardWhich constitutional isomer represents the product of this Diels-Alder reaction?arrow_forward
- Furan and maleimide undergo a Diels–Alder reaction at 25 °C to give the endo isomer of the product. When the reactiontakes place at 90 °C, however, the major product is the exo isomer. Further study shows that the endo isomer of theproduct isomerizes to the exo isomer at 90 °C.furan: O maleimide:OON H(a) Draw and label the endo and exo isomers of the Diels–Alder adduct of furan and maleimide.(b) Which isomer of the product would you usually expect from this reaction? Explain why this isomer is usually favored.(c) Examine your answer to (b) and determine whether this answer applies to a reaction that is kinetically controlled orone that is thermodynamically controlled, or both.(d) Explain why the endo isomer predominates when the reaction takes place at 25 °C and why the exo isomer predominates at 90 °Carrow_forward2) Rank the following dienes in order of increasing rate of Diels-Alder reaction with maleic anhydride. You do not need to explain your ranking. H3C. H3CO Diene A Diene B Diene Carrow_forwardChoose the correct option. 1. Which of the following reactions best describes the Diels-Alder reaction?A)electrocyclic reactionB)cycloaddition reactionC)sigmatropic reactionD)radical reactionE)nucleophilic substitution reaction 2.Which of the following statements best describes the theory of Conservation of Orbital Symmetry?A)Molecular orbital of the transition state must be similar to that of the reactant.B)Molecular orbital of the transition state must be similar to that of the product.C)Only s orbitals from reactants and products are utilized.D)Molecular orbitals of reactant and product must have similar symmetry.E)Molecular orbitals of reactant and product must have different symmetry. 3.Through what type of single pericyclic reaction did the reaction proceed? 5-methylcyclopenta-1,3-diene to 1-methylcyclopenta-1,3-dieneA)[1,2] sigmatropic hydrogen migrationB)[1,3] sigmatropic hydrogen migrationC)[1,4] sigmatropic hydrogen migrationD)[1,5] sigmatropic hydrogen migrationE)none of the…arrow_forward
- 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?arrow_forwardwhat is the product after these compumds undergo a diels-alder reactionarrow_forwardDraw the reactants that would react to form this cyclohexene derivative in a Diels-Alder reaction. Include any relevant stereochemical configurations. { Edit Diene + Draw Dienophile Qarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning