Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter 2007

Chapter 11 Skills

Aromaticity

Knowledge - Level 1

Terminology:

common names: toluene, cumene, styrene, phenol, aniline, anisole
benzoic acid, benzaldehyde
annulene, naphthalene, anthracene, phenanthrene
pyridine, pyrrole, furan, thiophene, pyrimidine, imidazole
group names: phenyl, benzyl
position names: ortho, meta, para, benzylic
aromaticity, Huckel's Rule


Concepts - Level 2

recognize aromaticity as special stability, with various implications, such as

show low reactivity compared to alkenes
do not undergo addition reactions like alkenes
show NMR ring current effects

recognize the special stability of intermediates at a benzylic position, based on resonance delocalization


Applications - Level 3

predict the expected patterns of MOs for various conjugated pi systems

write mechanisms for reactions at benzylic positions

write resonance forms for benzylic intermediates


Analytical Skills - Level 4 & higher

predict whether a given compound is aromatic, antiaromatic, or nonaromatic