Concept explainers
To determine: The structures of an intermediate and the final product, with particular attention to their stereochemistry.
Interpretation: The structures of the intermediate and the final product, with particular attention to their stereochemistry are to be predicted.
Concept introduction: Cycloaddition reactions involve the addition of two or more unsaturated cyclic molecules. There is no need of nucleophile and an electrophile in these types of reactions.
Stereochemistry is the branch of chemistry that deals with
Decarboxylation reaction involves the release of carbon dioxide to form a product through the removal of carboxyl group. The reverse process is known as carboxylic reaction.
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Organic Chemistry (9th Edition)
- Write a general rule that can be used to predict the major product of a Diels–Alder reaction between an alkene with an electron-withdrawing substituent and a diene with a substituent that can donate electrons by resonance depending on the location of the substituent on the diene.arrow_forwardThe Wittig reaction can be used for the synthesis of conjugated dienes, as, for example, 1-phenyl-1,3-pentadiene. -CH=CHCH CHCH, 1-Phenyl-1,3-pentadiene Propose two sets of reagents that might be combined in a Wittig reaction to give this conjugated diene.arrow_forwardGive the structure of the main product of each of the following Diels-Alder reactions. Make sureto show the stereochemistry of the products when unambiguous.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_forwardStep 6: Now that you have determined the substrates and mechanism of a Diels-Alder reaction, you will learn how to recognize when you should use the Diels-Alder reaction. In a synthesis reaction, if you are given a cyclohexene product with no other obvious functional group transformations and an electron-withdrawing group two carbons away from the alkene, it is likely made via the Diels-Alder reaction. Deduce the structures of the starting materials to form the Diels-Alder adduct shown. ..... CN CN Diene + Dienophilearrow_forwardAlthough the Diels–Alder reaction generally occurs between an electronrich diene and an electron-deficient dienophile, it is also possible to have inverse-demand Diels–Alder reactions between suitable electrondeficient conjugated double bonds and electron-rich alkenes. These reactions are particularly useful because they allow for the incorporation of heteroatoms into the new six-membered ring. Predict the products of each inverse-demand Diels–Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one regioisomer is possible, draw both.arrow_forward
- Bicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.arrow_forwardPredict the product(s) of the following Diels-Alder reaction. Include stereochemistry if appropriate.arrow_forwardThe highly reactive triple bond of benzyne is a powerful dienophile. Predict the productof the Diels–Alder reaction of benzyne (from chlorobenzene and NaOH, heated) withcyclopentadiene.arrow_forward
- The following compound undergoes an intramolecular Diels-Alder reaction to give a tricyclic product. Propose a structural formula for the product. heat An intramolecular Diels-Alder adductarrow_forwardA hetero Diels-Alder reaction is a variation of the Diels-Alder reaction in which one or more carbon atoms of the diene and/or the dienophile are replaced by other atoms such as oxygen or nitrogen. With this in mind, propose a mechanism consistent with the following transformation in which a multifunctional acyclic reactant produces a macrocyclic (large ring) product. 195°C. 2 Ph Ph- Ph IIarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning