Q: 9
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A: The major product for the given reaction is: dExplanation:
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A: This answer is given below. Explanation:
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- 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.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.The 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.
- Rank the following dienophiles in order of increasing reactivity.The 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.Complete the following by drawing products for a and b, and also identify the diene and dienophile in each one.
- 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?Rank the following dienes in order of increasing reactivity in a Diels-Alder reaction.The 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.
- Draw and discuss the mechanism (with arrows to show electron movements) of the Diels-Alder reaction between anthracene and maleic anhydride. Draw the orientation and phases of the reacting p-orbitals showing how they overlap in a “suprafacial” geometry to form productConsider the following dienes in a Diels–Alder reaction with ethene. Which will react the fastest? Which will react the slowest? ExplainRank the following in order from slowest to fastest rate of reaction in a Diels–Alder reaction with buta-1,3-diene