Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Which of the following compounds is antiaromatic?
Correct answer
2
Step-by-step solution
A compound is antiaromatic if it is cyclic, planar, fully conjugated, and contains 4n electrons ( n = 1, 2, 3, ). In option (A), the 1,3,2-dioxaborole ring has 2 electrons from the C=C bond and 4 electrons from the lone pairs of the two oxygen atoms, while boron has an empty p-orbital. Total electrons = 2 + 4 + 0 = 6 . It is aromatic ( 4n+2 rule). In option (B), oxazole has 4 electrons from two double bonds and 2 electrons from one lone pair of the oxygen atom. The nitrogen lone pair is localized in an sp^2 orbital