Organic Chemistry II |
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Professor Carl C. Wamser |
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Chem 335 - Winter 2006 |
Chapter 12 Skills |
Knowledge - Level 1
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