Chem 336 - Spring 2000
Organic Chemistry III

Dr. Carl C. Wamser


Chapter 19 Skills


Knowledge - Level 1

know the 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, Frost Circle


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 cyclic pi systems

write acid-base reactions for phenols, including aqueous extraction procedures

write typical reactions for phenols

write mechanisms for reactions at benzylic positions

use benzylic ethers as protecting groups


Analytical Skills - Level 4

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