Chem 335 - Winter 2002
Organic Chemistry II
Dr. Carl C. Wamser
Terminology:
activating, deactivating
substituent effects
directing effects
Friedel-Crafts reaction
partial rate factor
know the general reaction mechanism for electrophilic aromatic
substitution
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)
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 expected products from electrophilic aromatic substitution
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