Problem Set 2

1. Predict the stereochemistry of the thermal electrocyclic ring closure of (2E,4Z)-2,4-

hexadiene to 3,4-dimethyl-1,3-cyclobutene.

Use the concept of conservation of orbital symmetry to show if the reaction goes through a
disrotatory or conrotarory mode

2. State if the following electrocyclic reaction would occur readily by a concerted mechanism

heat

3. Show that using the HOMO from the 2π-electron component and the LUMO from the 4 π-
electron component also gives bonding overlap in a [4s+2s] cycloaddition.(consider the thermal
reaction)

4. Show by a frontier orbital analysis that the [4a+2s] and [4s+2a] modes of cycloaddition are
not allowed. .(consider the thermal reaction)

5. Give the product of the following reaction, which involves an [8s+2s] cycloaddition.