1a.) Draw the pi molecular orbitals for 1,3,5 hexatriene, show the electron population of each level,...

1a.) Draw the pi molecular orbitals for 1,3,5 hexatriene, show the electron population of each level, and identify the HOMO and the LUMO.

1b.) Show using drawings of the HOMO of the maleic and the LUMO of maleic anhydride that a [6+2] cycloaddition of 1,3,5 hexatriene and maleic anhydride is thermally forbidden.

1c.) The compound 1,3,5-hexatriene does undergo a [4+2] cycloaddition with maleic anhydride, however. Show the product that results from this reaction.

Solutions

Expert Solution

Answer-1) Pi-Molecular orbitals of 1,3,5-Hexatriene are shown in diagram. HOMO and LUMO also shown.

Answer-2) Cycloaddition reactions are kind of pericyclic reaction which is strictly governed by MO symmetry rule. Rule state that the MO with same symmetry only overlaps and this orbital symmetry is conserved in the product also. Based on this we can see in diagram that LUMO of Hexatriene and HOMO of maleic anhydride do not match at one side and hence it is [6+2] cycloaddition is thermally forbidden.

Answer-3) Yes, 1, 3, 5-Hexatriene can undergo [4+2] cycloaddition reaction as we can see in diagram. It’s a thermally allowed reaction and well known as Diels-Alder reaction.

queen_honey_blossom answered 1 year ago

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