Alec wanted to prepare to diene B to use in a subsequent Diels-Alder reaction. He thought he could prepare it via the reaction shown below. However, treatment of the diol (A) with acid yield either ketone (C) as the major product. H,SO, Но. Heat Ph Ph OH A B C a. Give a detail account of how you would determine whether product of the reaction was B or C. Assume that the only method available to you is FT-IR. You must give values for all features of all spectra. b. Provide a detail mechanism as to how compound B and Care formed under the reaction conditions. .

Alec wanted to prepare to diene B to use in a subsequent Diels-Alder reaction. He thought he could prepare it via the reaction shown below. However, treatment of the diol (A) with acid yield either ketone (C) as the major product. H,SO, Но. Heat Ph Ph OH A B C a. Give a detail account of how you would determine whether product of the reaction was B or C. Assume that the only method available to you is FT-IR. You must give values for all features of all spectra. b. Provide a detail mechanism as to how compound B and Care formed under the reaction conditions. .

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

See similar textbooks

Similar questions

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.
8) Predict the two products that form in following Diels-Alder reaction Circle the major product. CH₂O CH₂OCH, H O₂N
1) Provide the structure of the major product, which results from Diels-Alder reaction. + Diels-Alder Reaction
3. Show how Diels-Alder reactions might be used to synthesize the following compounds. a. H
Assume that the alkyne reacts with the diene in a Diels-Alder reaction. Use the JSME editor product of the reaction. The guide on how to draw your structure can be found here + to draw the structure of the
3) How would you form the following molecule using a Diels-Alder reaction?
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?
This 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.
Compounds P and Q can undergo a Diels-Alder reaction to form two regioisomeric products R and S as shown in Figure 5. OMe P H C8H1202 R C8H1202 S Figure 5 Draw the chemical structures of regioisomeric compounds R and S. (ii) Using possible resonance contributors of P and Q predict which of the two regioisomers will be favoured in the reaction. (iii) 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
2) A Diels-Alder reaction yields the following compound. Please write the structure of diene and dienophile, and synthesize the dienophile from a starting material with no more than four carbon. "CO₂Et
2. Aromaticity a. Which of the two nitrogens in the molecule below, the one in the upper ring or the one in the lower ring (or both, or neither) is basic? Explain your answer b. Prof. Fresser, using a Diels-Alder-type reaction, attempted to make the molecule below, hoping it would be aromatic. Leaving aside whether the synthesis would work, explain whether the molecule below would be aromatic. a b