Organic Chemistry II |
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Professor Carl C. Wamser |
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Chem 335 - Winter Term |
Chapter 12 Skills |
Knowledge - Level 1
Terminology:
activating, deactivating
substituent effects
directing effects
Friedel-Crafts reaction
partial rate factor
benzyne
know the general reaction mechanisms for electrophilic and nucleophilic aromatic substitution
recognize the effect of substituents in stabilizing or destabilizing an intermediate
carbocation or carbanion (activating or deactivating effects)
recognize the directing effects of substituents as a special case of stabilizing
or destabilizing an intermediate (ortho, para- or meta-directors)
understand the differences in structure and reactivity between alkyl halides and aryl halides
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 or nucleophilic 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