Chem 336 - Spring 1999 - Organic Chemistry III
Portland State University - Dr. Carl C. Wamser
Chapter 20 Skills
know the terminology:
activating, deactivating
substituent effects
Friedel-Crafts reaction
benzyne
Meisenheimer complex
know the general reaction mechanism for electrophilic aromatic
substitution, nucleophilc aromatic substitution, and substitution
via benzyne
recognize the effect of substituents in stabilizing or destabilizing
an intermediate carbocation (activating or deactivating effects)
recognize the directing effects of substituents as a special case
of stabilizing or destabilizing an intermediate carbocation (ortho,
para- or meta-directors)
recognize the effect of electron-withdrawing substituents in stabilizing an intermediate anion in nucleophilc aromatic substitution
identify the various strong electrophiles (and how they are generated) for different electrophilic aromatic substitution reactions:
bromination (Br+ from Br2 + FeBr3)
chlorination (Cl+ from Cl2 + FeCl3)
nitration (NO2+ from HNO3 + H2SO4)
sulfonation (SO3H+ from SO3 + H2SO4)
alkylation (R+ from RCl + AlCl3)
acylation (RCO+ from RCOCl + AlCl3)
be able to generate the resonance forms of an intermediate
benzenium ion
(including in the presence of an existing substituent on the ring)
identify products from electrophilic aromatic substitution, nucleophilc aromatic substitution, or substitution via benzyne
classify substituents based on their electron donating or
withdrawing characteristics
explain why a given substituent acts as activating or deactivating
explain why a given substituent acts as an ortho, para- director
or a meta-director
design a synthetic sequence for a given target compound, typically starting from benzene