The structure of the product with molecular formula C 17 H 16 O 6 formed when the triene shown reacts with 2 equivalents of maleic anhydride is to be given. Concept introduction: The reaction given involves two Diels-Alder reactions. In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. These reactions occur rapidly with dienophiles having electron withdrawing substituent groups in conjugation with the double bond and if the diene adapts a s-cis conformation during the reaction. To give: The structure of the product with molecular formula C 17 H 16 O 6 formed when the triene shown reacts with 2 equivalents of maleic anhydride.

Question

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?

Answer 1

Question

Chapter 14.SE, Problem 57AP

Interpretation Introduction

Interpretation:

The structure of the product with molecular formula C₁₇H₁₆O₆ formed when the triene shown reacts with 2 equivalents of maleic anhydride is to be given.

Concept introduction:

The reaction given involves two Diels-Alder reactions. In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. These reactions occur rapidly with dienophiles having electron withdrawing substituent groups in conjugation with the double bond and if the diene adapts a s-cis conformation during the reaction.

To give:

The structure of the product with molecular formula C₁₇H₁₆O₆ formed when the triene shown reacts with 2 equivalents of maleic anhydride.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

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?

The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.

The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formulaC5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.