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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: Using the Woodward鈥揌offmann rules in Table 27.4, predict the stereochemistry of each reaction.

a. a [6 + 4] thermal cycloaddition

b. photochemical electrocyclic ring closure of deca-1,3,5,7,9-pentaene

c. a [4 + 4] photochemical cycloaddition

d. a thermal [5,5] sigmatropic rearrangement

Question: Draw a stepwise, detailed mechanism for the following reaction.

Question:Using orbital symmetry, explain why a Diels鈥揂lder reaction does not take place under photochemical reaction conditions.

Question: What product is formed by the [3,3] sigmatropic rearrangement of each compound?

Question: Show how the following starting material is converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.
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