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Interpretation:
The given diene and dienophilethat are used in the synthesis of the productare to be determined.
Concept introduction:
The Diels–Alder reaction is the reaction between a conjugated diene and a compound containing double bond. i.e. a dienophile.
In theDiels–Alder reaction, two sigma bonds are formed from the expansion of the pi bond of the diene and dienophile. In this reaction the reactants are a diene and a dienophile out of whichtwo sigma bonds and one pi bond formation takes place.
The Diels–Alder reaction is stereospecific and the reaction is syn addition and the dienophile retains the configuration in the product.
Cyclic diene in which double bonds are in cis conformation are usually highly reactive in the Diels–Alder reaction.
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Chapter 13 Solutions
Organic Chemistry
- Intramolecular Diels–Alder reactions are possible when a substrate contains both a 1,3-diene and a dienophile, as shown in the following general reaction.With this in mind, draw the product when each compound undergoes an intramolecular Diels–Alder reaction.arrow_forwardHow many monohalogenation products can be obtained from the following compounds?arrow_forwardThe following diene does not undergo a Diels-Alder reaction with maleic anhydride, both in thermal and photochemical conditions. Explain why this reaction does not occur.arrow_forward
- Diphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo-1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene.(a) What is the structure, including stereochemistry, of the vinylic bromide?(b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?arrow_forwardThe following Diels-Alder reaction product is an intermediate in the synthesis of cholesterol. Provide the structure of the major product. Show stereochemistry when applicable. Hint: there are two possible dienophiles, which one is the better dienophile? Provide a brief explanation of your choice. CH,O.arrow_forwardIntramolecular Diels-Alder reactions are possible when a substrate contains both a 1,3-diene and a dienophile, as shown in the following general reaction. , two new rings With this in mind, draw the product of the following intramolecular Diels-Alder reaction. draw structure .arrow_forward
- How could the following compounds be synthesized using a Diels–Alder reaction?arrow_forwardDraw the diene and dienophile (the starting materials) to produce the following compound.arrow_forwardWhich substrate (or substrates) would not be good for a Friedel-Crafts reaction with AlCl3 as catalyst: ethyl bromide, chlorobenzene, allyl chloride, chlorocyclohexanearrow_forward
- Which of the following conjugated dienes will not react with a dienophile in a Diels–Alder reaction?arrow_forwardWhich of the following would be the best diene for a Diels - Alder cycloaddition reaction? A B C D Which of the following would be the best diene for a Diels-Alder cycloaddition reaction? A G A B C D B Uarrow_forwardwhat structure show the transition state for the rate determining step in the sn1 reaction with this picture?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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