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Chapter 27: Q 3. (page 1080)

Question: (a) Using Figure 27.2 as a guide, draw the molecular orbitals for hexa-2,4-diene. (b) Label the HOMO and the LUMO in the ground state. (c) Label the HOMO and the LUMO in the excited state.

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01

HOMO and LUMO

The high-energy molecular orbital that contains the electron pair is referred to as the highest occupied molecular orbital (HOMO).

The lowest molecular orbital that does not contain an electron pair is referred to as the lowest unoccupied molecular orbital (LUMO).

02

Structure of hexa-2,4-diene

hexa-2,4-diene

Hexadiene consists of two pi bonds that are made by the overlap of four p orbitals.

03

Molecular orbital diagram of hexa-2,4-diene

Molecular diagram of hexa-2,4-diene

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Most popular questions from this chapter

Question: Draw the product of each electrocyclic reaction.

a. the thermal electrocyclic ring closure of (2E,4Z,6Z)-nona-2,4,6-triene

b. the photochemical electrocyclic ring closure of (2E,4Z,6Z)-nona-2,4,6-triene

c. the thermal electrocyclic ring-opening of cis-5-ethyl-6-methylcyclohexa-1,3-diene

d. the photochemical electrocyclic ring-opening of trans-5-ethyl-6-methylcyclohexa-1,3- diene

Question: The endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rain forests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resulting conjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.

Question: What product is formed when each compound undergoes thermal electrocyclic ring opening or ring closure? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds.

Question:Draw the product (including stereochemistry) formed from each pair ofreactants in a thermal [4 + 2] cycloaddition reaction.

Question: Draw the product formed (including stereochemistry) in each pericyclic reaction.
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